Water → 5-Hydroxy-5-propyl-2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrol-1-one

HRID 1887498Notes

Reaction equation

[CH2:1]([Mg]Br)[CH2:2][CH3:3].[F:6][C:7]([F:26])([F:25])[O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH:18]3[CH2:20][C:21](=[O:23])[CH2:22][CH:17]3[C:16]2=[O:24])=[CH:11][CH:10]=1.O>C1COCC1>[OH:23][C:21]1([CH2:1][CH2:2][CH3:3])[CH2:22][CH:17]2[C:16](=[O:24])[N:15]([C:12]3[CH:13]=[CH:14][C:9]([O:8][C:7]([F:6])([F:25])[F:26])=[CH:10][CH:11]=3)[CH2:19][CH:18]2[CH2:20]1

Participants

Conditions

Temperature: 35 °C

Procedure

Propylmagnesium bromide (0.2 mL, 0.6 mmol, 3M) was added to a solution of 2-(4-trifluoromethoxy-phenyl)-hexahydro-cyclopenta[c]pyrrole-1,5-dione (0.1 g, 0.33 mmol) in THF (10 mL), and the mixture was stirred for 3 h at room temperature and overnight at 35° C. The solution was cooled, then poured into water (25 mL) and extracted with ether (3×20 mL), dried over Na2SO4. The solvent was removed and the residue was purified by prep-TLC (petroleum/ethyl acetate=1:1) to yield the title compound (25 mg, 21%). 1H NMR (300 MHz, CDCl3): δ 7.62-7.60 (m, 2H), 7.32-7.23 (m, 2H), 4.11 (t, 1H, J=9.5 Hz), 3.71-3.67 (m, 1H), 3.18 (t, 1H, J=9.5 Hz), 2.95 (d, 1H, J=9.6 Hz), 2.25-2.21 (m, 1H), 1.98-1.88 (m, 2H), 1.81-1.76 (m, 1H), 1.61-1.34 (m, 4H), 0.95 (t, 3H, J=7.2 Hz); LC-MS: 344.2 [M+1]+.

Workup

temperatureThe solution was cooled
extractionextracted with ether (3×20 mL)
dry with materialdried over Na2SO4
customThe solvent was removed
customthe residue was purified by prep-TLC (petroleum/ethyl acetate=1:1)

Sources & evidence

ORD record: ord-50db19aa68394f50b06ced6538423e35
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501768B2

Reaction notes

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