Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [CH2:1]([C:8]1([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:12][CH2:11][O:10][C:9]1=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[CH2:1]([C:8]1([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20])[CH2:12][CH2:11][O:10][CH:9]1[OH:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
Reactant: CC(C)(C)OC(=O)NC1(Cc2ccccc2)CCOC1=O
Agent: CC(C)C[AlH]CC(C)C
Solvent: C1CCOC1
Product: CC(C)(C)OC(=O)NC1(Cc2ccccc2)CCOC1O
Temperature: -78 °C
Reaction time: 5 h

Procedure:
To a solution of tert-butyl (3-benzyl-2-oxotetrahydrofuran-3-yl)carbamate (4.18 g, 14.3 mmol) in THF (100 mL) cooled to −78° C. was added DIBAL-H (57.4 mL, 57.4 mL, 1M hexane) dropwise over 15 min. The reaction mixture was stirred at −78° C. for 5 h, quenched with EtOAc, diluted with diethyl ether and aqueous Rochelle's salt. Vigorous stirring was allowed until gel break-up and layer formation. The organic layer was extracted, washed with aqueous Rochelle's salt, water, brine, dried over sodium sulfate, concentrated in vacuo, and purified by flash chromatography (120 g silica gel, 0 to 40% EtOAc in hexane) to give tert-butyl (3-benzyl-2-hydroxytetrahydrofuran-3-yl)carbamate (intermediate I) as a white foam (ca. 1:1 diastereomeric ratio). 1H NMR (400 MHz, CDCl3) δ 7.35-7.12 (m, 5H), 5.35 (s, 0.5H), 5.32 (s, 0.5H), 5.97 (s, 0.5H), 4.25 (s, 0.5H), 4.20-4.08 (m, 1H), 4.00-3.86 (m, 1H), 3.48-2.88 (m, 3H), 2.28-1.84 (m, 2H), 1.49 (s, 4.5H), 1.47 (s, 4.5H). MS M+Na=316.
Reaction SMILES: C([O:4][C:5]([C:7]1([C:18]2([NH:21][C:22](=[O:29])[CH2:23][C:24]([O:26][CH2:27]C)=[O:25])[CH2:20][CH2:19]2)[CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8]1)=O)(C)C.[Na]>C1(C)C=CC=CC=1.CO>[CH3:27][O:26][C:24]([CH:23]1[C:22](=[O:29])[NH:21][C:18]2([CH2:19][CH2:20]2)[C:7]2([CH2:8][N:9]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:10]2)[C:5]1=[O:4])=[O:25]
Reactant: CCOC(=O)CC(=O)NC1(C2(C(=O)OC(C)C)CN(C(=O)OC(C)(C)C)C2)CC1
Agent: [Na]
Solvent: CO
Solvent: Cc1ccccc1
Product: COC(=O)C1C(=O)NC2(CC2)C2(CN(C(=O)OC(C)(C)C)C2)C1=O
Temperature: 85 °C

Procedure:
The mixture of 3-[1-(2-ethoxycarbonyl-acetylamino)-cyclopropyl]-azetidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-isopropyl ester and ethyl ester (Example 180b) (350 mg; 0.35 mmol) is dissolved in toluene (5 ml) and added dropwise under stirring to a solution of sodium (20 mg; 0.85 mol) in MeOH (1 ml). The mixture is heated to 85° C. for 45 minutes, cooled, and the resulting suspension (Na-salt of title compound) filtered, washed with toluene and isopentane. The white solid is taken up in water/2N HCl (20 ml/0.5 ml) and extracted with CH2Cl2 three times. The combined organic phases are dried over Na2SO4, filtered and evaporated to dryness to deliver the title compound as almost colorless foam (166 mg; 58%).