Sodium borohydride → (3aS,4S,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ol

HRID 2363446Notes

Reaction equation

[CH2:1]([N:8]1[CH2:12][C@H:11]2[C:13](=[O:16])[CH2:14][CH2:15][C@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([N:8]1[CH2:12][C@H:11]2[C@@H:13]([OH:16])[CH2:14][CH2:15][C@H:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -40 °C

Procedure

A mixture of (3aS,6aR)-2-benzylhexahydrocyclopenta[c]pyrrol-4(5H)-one (1.462 g, 6.79 mmol) from Step A in methanol (20 mL) was cooled in an dry ice/acetone bath to −40° C. Sodium borohydride (0.514 g, 13.58 mmol) was added in portions over 5 minutes. The reaction allowed to warm to room temperature overnight, then it was quenched with saturated aqueous ammonium chloride, diluted with water, and extracted with 3×150 mL of ethyl acetate. The combined extracts were dried (Na2SO4) and the solvent was removed in vacuo to give (3aS,4S,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ol: 1H NMR (300 MHz, CDCl3) δ ppm 7.38-7.16 (m, 5H), 4.21-4.04 (m, 1H), 3.66 (d, J=12.8, 1H), 3.51 (d, J=12.8, 1H), 3.07 (d, J=9.3, 1H), 2.65-2.53 (m, J=11.8, 2H), 2.52-2.43 (m, 1H), 2.18-2.07 (m, J=7.5, 16.3, 2H), 2.05-1.94 (m, J=8.7, 12.6, 1H), 1.84-1.74 (m, J=6.2, 1H), 1.49-1.34 (m, 3H).

Workup

temperatureto warm to room temperature overnight
customit was quenched with saturated aqueous ammonium chloride
additiondiluted with water
extractionextracted with 3×150 mL of ethyl acetate
dry with materialThe combined extracts were dried (Na2SO4)
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-de9ffe27a5404a2d8f65dfc6a5256c1e
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691865B2

Reaction notes

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