Sodium borohydride → HCID 86659850, compound
Reaction equation
[N:1]1([CH:6]2[CH2:20][C@@H:9]3[CH2:10][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][C@@H:8]3[C:7]2=[O:21])[CH:5]=[CH:4][N:3]=[CH:2]1.[BH4-].[Na+]>CO>[OH:21][CH:7]1[C@@H:8]2[C@@H:9]([CH2:10][N:11]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:12]2)[CH2:20][CH:6]1[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
(3aR,6aS)-tert-Butyl 5-(1H-imidazol-1-yl)-4-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (75 mg, 0.257 mmol) from Step 2 in methanol (2 mL) was cooled in a dry ice/acetone bath to −78° C., and sodium borohydride (11.69 mg, 0.309 mmol) was added. The reaction was allowed to warm to ambient temperature over 6 hours. Then the reaction mixture was partially concentrated, quenched with 10 mL of aqueous ammonium chloride, diluted with water, and extracted with 2×20 mL of ethyl acetate. The extracts were washed with brine, dried (Na2SO4) and filtered. The solvent was removed in vacuo. The crude product was purified using a 4 g silica gel cartridge with a gradient of 0-6% CH3OH (2 N NH3)/CH2Cl2 over 20 minutes to give (3aR,6aS)-tert-butyl 4-hydroxy-5-(1H-imidazol-1-yl)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate.