Reaction SMILES: [NH2:1][C:2]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)=[CH:32][CH:31]=1)=[CH:3][C:4](=[O:28])[C@@H:5]([N:13]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CS(O)(=O)=O.O([BH-](OC(C)=O)OC(C)=O)C(C)=O.[Na+].N(CCO)(CCO)CCO.[BH4-].[Na+]>ClCCl.O.C(O)(C)C.CC(N(C)C)=O>[NH2:1][C@@H:2]([CH2:29][C:30]1[CH:31]=[CH:32][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=2)=[CH:34][CH:35]=1)[CH2:3][C@H:4]([OH:28])[C@@H:5]([N:13]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1
Reactant: NC(=CC(=O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1)Cc1ccc(-c2ccccn2)cc1
Agent: CC(=O)O[BH-](OC(C)=O)OC(C)=O
Agent: CS(=O)(=O)O
Agent: [BH4-]
Solvent: O
Solvent: OCCN(CCO)CCO
Solvent: ClCCl
Product: N[C@@H](Cc1ccc(-c2ccccn2)cc1)C[C@H](O)[C@H](Cc1ccccc1)N(Cc1ccccc1)Cc1ccccc1
Temperature: -16 °C
Reaction time: 1 h
Yield: 76.5 %

Procedure:
To a jacketed round bottom 1L flask was added 27.5 g (1 eq) of the product of Example 2-1, 300 mL of dimethylacetamide and 30 mL of isopropyl alcohol. The reaction solution was cooled to about −16° C. and treated with 33 mL (10 eq) of methanesulfonic acid slowly (The reaction was exothermal, temperature raised to 9° C.). The mixture was cooled to about −16° C., treated with 54.1 g (5 equivalents) of sodium triacetoxylborohydride. Mixed at −16° C. for about 2 hrs and 30 min, HPLC showed the first reduction was completed. 67.9 mL (10 equivalents) of triethanolamine was then added slowly (exothermal). The mixture was stirred at about −16° C. for 1 hr. 7.7 g of sodium borohydride was added in 7 portions. The reaction mixture was stirred at −16° C. until the reduction was completed as indicated by HPLC (Column: YMC QDS-AQ 15 cm, flow 1 ml/1 min, Gradient system: 0-15 min, 80% 0.03M HK2PO4/20% CH3CN/to 20% 0.03M HK2PO4/80% CH3CN, 15-20 hold at 20% 0.03M HK2PO4/80% CH3CN, 20-21 min, 20% 0.03M HK2PO4/80% CH3CN to 80% 0.03M HK2PO4/20% CH3CN, 21-23 min, hold at 80% 0.03M HK2PO4/20% CH3CN), treated with 100 mL of water, stirred at room temperature overnight and diluted with 300 mL of dichloromethane to the reaction mixture. The isolated dichloromethane layer (Assay: 23 g, yield: 83.5%. ds: 95% as measured by HPLC (Column: YMC QDS-AQ 15 cm, flow 1 ml/1 min, Gradient system: 0-15 min, 80% 0.03M HK2PO4/20% CH3CN/ to 20% 0.03M HK2PO4/80% CH3CN, 15-20 hold at 20% 0.03M HK2PO4/80% CH3CN, 20-21 min, 20% 0.03M HK2PO4/80% CH3CN to 80% 0.03M HK2PO4/20% CH3CN, 21-23 min, hold at 80% 0.03M HK2PO4/20% CH3CN) was extracted with 0.3% H3PO4 solution (3×200 mL). The pH of the isolated aqueous layer was adjusted to 6-7 with sodium carbonate. The resulting solution was extracted with dichloromethane (2×300 ml). The combined isolated dichloromethane layers were washed with 200 mL of 5% aqueous KH2PO4, dried (Na2SO4) and concentrated. The resulting residue was dissolved in 100 mL of isopropyl acetate and washed sequentially with 100 mL of 5% KH2PO4 and brine. The isopropyl acetate solution was concentrated and 21.2 g of the title compound was obtained as a yellow foam.