Ammonium Chloride → Tert-butyl 3-(1-hydroxy-5-methoxy-1-phenylpentyl)pyrrolidine-1-carboxylate

HRID 253552Notes

Reaction equation

[C:1]([CH:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][O:22][CH2:23][CH2:24][CH2:25][CH2:26][Mg]Cl.[NH4+].[Cl-]>C1COCC1>[OH:8][C:1]([CH:9]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]1)([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:26][CH2:25][CH2:24][CH2:23][O:22][CH3:21]

Participants

Conditions

Temperature: -70 °C

Procedure

A stirred solution of tert-butyl 3-benzoylpyrrolidine-1-carboxylate (489 mg, 1.78 mmol) in dry THF (10 mL) was cooled to −70° C. and 2 M 4-methoxybutylmagnesium chloride in THF (8 mL, 16 mmol) was added. The mixture was stirred at −70° C. for 1 h and poured into satd aq NH4Cl (100 mL). The mixture was extracted with ether (2×100 mL) and the combined ether extracts were dried over Na2SO4. Removal of the solvent left an oil which was purified by flash chromatography on a 40-g silica cartridge eluted with a 0 to 100% ethyl acetate in hexanes gradient to afford tert-butyl 3-(1-hydroxy-5-methoxy-1-phenylpentyl)pyrrolidine-1-carboxylate (290 mg, 44%).

Workup

extractionThe mixture was extracted with ether (2×100 mL)
dry with materialthe combined ether extracts were dried over Na2SO4
customRemoval of the solvent
waitleft an oil which
customwas purified by flash chromatography on a 40-g silica cartridge
washeluted with a 0 to 100% ethyl acetate in hexanes gradient

Sources & evidence

ORD record: ord-4012d03427a04d28a4a247d17b6de104
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872028B2

Reaction notes

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