Reaction SMILES: O.[N-:2]=[N+:3]=[N-:4].[Na+].[Cl-].[NH4+].[F:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C@H:17]([CH2:18][O:19][CH2:20][O:21][CH3:22])[NH:16]2)=[CH:11][CH:10]=1>CN(C)C=O>[N:2]([C:15]([C:12]1[CH:13]=[CH:14][C:9]([F:8])=[CH:10][CH:11]=1)([C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[C@@H:17]([NH2:16])[CH2:18][O:19][CH2:20][O:21][CH3:22])=[N+:3]=[N-:4]
Reactant: COCOC[C@@H]1NC1(c1ccc(F)cc1)c1ccc(F)cc1
Reactant: [N-]=[N+]=[N-]
Agent: [Cl-]
Agent: [NH4+]
Agent: [Na+]
Solvent: O
Solvent: CN(C)C=O
Product: COCOC[C@H](N)C(N=[N+]=[N-])(c1ccc(F)cc1)c1ccc(F)cc1
Temperature: 100 °C
Reaction time: 16 h
Yield: 87.4 %

Procedure:
While stirring a solution of methyl (2S)-2-{[(benzyloxy)carbonyl]amino}-3-(methoxymethoxy)-propanoate (35.70 g) in tetrahydrofuran (500 mL) under nitrogen at 0° C., 1.0M 4-fluorophenylmagnesium bromide-tetrahydrofuran solution was added to the solution dropwise. Temperature of the mixture was raised to room temperature, and then the mixture was stirred for 4 hours. Saturated ammonium chloride aqueous solution (100 mL) was added to the reaction mixture, and then the reaction mixture was concentrated in vacuo. Saturated ammonium chloride aqueous solution was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution in this order and dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration, and then the organic solvent was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (C-300; hexane:ethyl acetate=9:1→5:1→3:1) to give benzyl N-{(1S)-2,2-bis(4-fluorophenyl)-2-hydroxy-1-[(methoxymethoxy)methyl]ethyl}carbamate (49.97 g) as colorless oil. The product (49.80 g) was stirred in the presence of 10% palladium carbon catalyst (2.00 g) in methanol solvent (500 mL) under 1 atm hydrogen for two days, and reaction mixture was heated up to 50° C. and stirred for 24 hours. The reaction mixture was filtered through celite, and then the obtained filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (C-300; hexane:ethyl acetate=2:1→chloroform:methanol=5:1) to give (2S)-2-amino-1,1-bis(4-fluorophenyl)-3-(methoxymethoxy)-1-propanol (33.30 g) as yellow oil. While stirring a solution of triphenylphosphine (40.56 g) in toluene (400 mL) at 0° C., 1.0M bromine-benzene solution was added to the solution dropwise, and the mixture was stirred for 30 minutes. A solution of the above-mentioned hydroxyamine compound (20.00 g) in toluene (50 mL) and triethylamine (43.11 g) were dropwise added at 0° C. in this order. Thereafter the reaction mixture was stirred at 0° C. for 20 hours, and saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture. The resultant mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration, and then the organic solvent was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (C-300; hexane:ethyl acetate=4:1→2:1) to give (3R)-2,2-bis(4-fluorophenyl)-3-[(methoxymethoxy)methyl]aziridine (7.72 g) as yellow oil. Water (40 mL), sodium azide (7.45 g) and ammonium chloride (2.70 g) were added in this order to a solution of the aziridine compound (7.70 g) in N,N-dimethylformamide (80 mL), and the mixture was stirred at 100° C. for 16 hours. Moreover, sodium azide (7.45 g) was added to the reaction mixture, and the mixture was stirred at 120° C. for 24 hours. Thereafter water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer was washed with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution in this order and dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration, and then the organic solvent was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (C-300; hexane:ethyl acetate=3:1) to give (2R)-1-azido-1,1-bis(4-fluorophenyl)-3-(methoxymethoxy)-2-propanamine (7.68 g) as yellow oil. The obtained azide compound (7.62 g) was stirred in the presence of 5% palladium carbon catalyst (0.80 g) in methanol solvent (80 mL) under 1 atm hydrogen for 17 hours. The reaction mixture was filtered through celite and washed with ethyl acetate. The obtained filtrate was washed with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution in this order and dried over anhydrous sodium sulfate. Sodium sulfate was removed by filtration, and then the organic solvent was evaporated in vacuo. The obtained residue was purified by silica gel column chromatography (C-300; ethyl acetate→chloroform:methanol=5:1) to give the title diamine (5.70 g) as pale yellow oil.