Aluminium lithium hydride → Tert-butyl 1-benzyl-3-(hydroxymethyl)pyrrolidin-3-ylcarbamate

HRID 339017Notes

Reaction equation

[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([C:13](OC)=[O:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([NH:17][C:18](=[O:19])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])([CH2:13][OH:14])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 1-benzyl-3-(tert-butoxycarbonylamino)pyrrolidine-3-carboxylate (21.7 g, 64.9 mmol) in THF (320 mL) was added dropwise a solution of LiAlH4 in THF (1.0 M, 55.2 mL, 55.2 mmol) at −78° C. under nitrogen. The reaction mixture was warmed to 0° C. for 5 minutes and then quenched by dropwise addition of water (2.1 mL) followed by 15% NaOH (2.1 mL) and water (6.3 mL). The reaction mixture was stirred at ambient temperature for 15 minutes and then filtered through Celite®. The filtrate was concentrated under reduced pressure and purified by flash chromatography on silica gel (4% MeOH in DCM) to give tert-butyl 1-benzyl-3-(hydroxymethyl)pyrrolidin-3-ylcarbamate (11.2 g, 56%) as a colorless oil.

Workup

customquenched by dropwise addition of water (2.1 mL)
filtrationfiltered through Celite®
concentrationThe filtrate was concentrated under reduced pressure
custompurified by flash chromatography on silica gel (4% MeOH in DCM)

Sources & evidence

ORD record: ord-ac6a51f66c304c0098aa46e668e4e475
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889704B2

Reaction notes

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