Sodium borohydride → HCID 66996649, compound

HRID 2402745Notes

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 (3aR,6aS)-2-benzylhexahydrocyclopenta[c]pyrrol-4(5H)-one (1.462 g, 6.79 mmol) in methanol (20 mL) was cooled in a 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 the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 7.45-7.38 (m, 2H), 7.34 (dd, J=10.2, 4.7, 2H), 7.30-7.24 (m, 1H), 5.63 (s, 1H), 4.30 (dd, J=11.4, 6.2, 1H), 3.54 (q, J=13.0, 2H), 3.17 (dd, J=9.3, 3.3, 1H), 2.57 (dtd, J=10.0, 7.1, 3.2, 1H), 2.48 (dtt, J=17.5, 8.7, 4.3, 1H), 2.44-2.38 (m, 2H), 2.31 (dd, J=9.2, 7.4, 1H), 2.04-1.96 (m, 1H), 1.76-1.61 (m, 2H), 1.47-1.40 (m, 1H); MS (ESI+) m/z 217 (M+H)+.

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-21cf3b94f28f44328bd1a56eec152d87
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796470B2

Reaction notes

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