Trifluoroacetic acid → 3-Methylazetidine-3-carbonitrile; trifluoroacetic acid

HRID 1898507Notes

Reaction equation

HRID 1898507 reaction equation
C(OC([N:8]1[CH2:11][C:10]([C:13]#[N:14])([CH3:12])[CH2:9]1)=O)(C)(C)C.[F:15][C:16]([F:21])([F:20])[C:17]([OH:19])=[O:18]>ClCCl>[F:15][C:16]([F:21])([F:20])[C:17]([OH:19])=[O:18].[C:13]([C:10]1([CH3:12])[CH2:11][NH:8][CH2:9]1)#[N:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 56971684tert-Butyl 3-cyano-3-methylazetidine-1-carboxylate

Product 1

HCID 673862343-Methylazetidine-3-carbonitrile; trifluoroacetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Cyano-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.23 g, 1.17 mmol) was dissolved in 12 mL of dichloromethane and the reaction was then stirred in an ice bath. Trifluoroacetic acid (3.6 mL) was added slowly and the solution was warmed to room temperature. After 3 h the reaction mixture was evaporated to afford 3-cyano-3-methyl-azetidine trifluoroacetate which was used without further purification.

Workup

  1. customAfter 3 h the reaction mixture was evaporated

Sources & evidence

ORD record
ord-45e78b1486e74e1face942ff5f37f8b0
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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