N-Fluorobenzenesulfonimide → Methyl (3R)-3-(4-chlorophenyl)-3-cyclopropyl-2-fluoropropanoate

HRID 1835035Notes

Reaction equation

C([N-]C(C)C)(C)C.[Li+].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]([CH:22]2[CH2:24][CH2:23]2)[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:12][CH:11]=1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:35])(=O)=O)=CC=1>O1CCCC1>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([C@@H:16]([CH:22]2[CH2:23][CH2:24]2)[CH:17]([F:35])[C:18]([O:20][CH3:21])=[O:19])=[CH:14][CH:15]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a stirred solution of lithium diisopropyl amide (30 mmol) in dry tetrahydrofuran (125 ml) under nitrogen at −78° C. is added dropwise a solution of methyl (3R)-3-(4-chlorophenyl)-3-cyclopropylpropanoate (6.5 g, 27.2 mmol) in dry tetrahydrofuran (50 ml). The reaction mixture is allowed to warm to 0° over 5 minutes, re-cooled to −78° C., and N-fluorobenzenesulfonimide (19.1 g, 60.6 mmol) is added.

Workup

temperatureto warm to 0° over 5 minutes

Sources & evidence

ORD record: ord-7cb6eeccfdf142ff92f2282a8200dc30
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06770463B2

Reaction notes

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