(R)-tert-butyl 4,4-difluoro-2-(4-methyl-2-oxopent-3-enyl)pyrrolidine-1-carboxylate → 1-((R)-4,4-difluoropyrrolidin-2-yl)-4-methylpent-3-en-2-one

HRID 633348Notes

Reaction equation

HRID 633348 reaction equation
[F:1][C:2]1([F:21])[CH2:6][N:5](C(OC(C)(C)C)=O)[C@H:4]([CH2:14][C:15](=[O:20])[CH:16]=[C:17]([CH3:19])[CH3:18])[CH2:3]1>C(O)=O>[F:21][C:2]1([F:1])[CH2:6][NH:5][C@H:4]([CH2:14][C:15](=[O:20])[CH:16]=[C:17]([CH3:18])[CH3:19])[CH2:3]1

Participants

3

Reactant 1

HCID 86704458(R)-tert-butyl 4,4-difluoro-2-(4-methyl-2-oxopent-3-enyl)pyrrolidine-1-carboxylate

Product 1

HCID 867044601-((R)-4,4-difluoropyrrolidin-2-yl)-4-methylpent-3-en-2-one

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A HCO2H (20 ml) solution of (R)-tert-butyl 4,4-difluoro-2-(4-methyl-2-oxopent-3-enyl)pyrrolidine-1-carboxylate (1.10 g, 3.6 mmol) was stirred at room temperature for 6 hours until only trace amount of SM was detected by LC-MS. Solvent was removed in vacuo with bath temperature≦23° C. Compound 1-((R)-4,4-difluoropyrrolidin-2-yl)-4-methylpent-3-en-2-one was obtained as a light brown oil and was used directly in next reaction.

Workup

  1. customSolvent was removed in vacuo with bath temperature≦23° C

Sources & evidence

ORD record
ord-53fa5954fe544d48a6c51b7d253c6446
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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