Sodium borohydride → tert-butyl N-[3-(hydroxymethyl)cyclohexyl]carbamate
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15](OC)=[O:16])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C1COCC1.CO.C(Cl)Cl>[OH:16][CH2:15][CH:11]1[CH2:12][CH2:13][CH2:14][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10]1Participants
4
Procedure
To a solution of methyl 3-(tert-butoxycarbonylamino)cyclohexanecarboxylate (9 mmol) in THF/MeOH/CH2Cl2 (36 ml, 10:1:1) was added NaBH4 (22.5 mmol) and stirred at rt overnight. The reaction was quenched with water and extracted with CH2Cl2 (3×10 mL). The extracts were combined and dried using anhydrous sodium sulfate. The product was purified using Biotage.