Tert-butyl 3-oxopyrrolidine-1-carboxylate → HCID 67403422, compound

HRID 1931863Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[F:9].[C:10]([N:17]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]>C(OCC)C>[F:9][C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[C:19]1([OH:22])[CH2:20][CH2:21][N:17]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:18]1

Participants

Conditions

Temperature: -78 °C

Procedure

Preparation according to Preparation 23: 1-bromo-2,3-difluorobenzene (3.12 g, 16.2 mmol), dry diethyl ether (30 mL), N-butyl lithium (2.5 M, 6.5 mL, 16.2 mmol), 1-N-boc-3-pyrrolidinone (2.0 g, 10.8 mmol). Stirred 2 h at −78° C. before addition, and 1 h at ambient temperature after addition of 1-N-boc-3-pyrrolidinone. Yield: 1.72 g. MS m/z (rel. intensity, 70 eV) 299 (M+, 1), 243 (46), 226 (38), 198 (68), 57 (bp).

Workup

customPreparation
customaccording to Preparation 23

Sources & evidence

ORD record: ord-3f8c13eb3fcd4cfaa27ac39ebcf521f3
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188301B2

Reaction notes

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