Trifluoroacetic acid → 3-Butoxy-3-o-tolylazetidine trifluoroacetate

HRID 540414Notes

Reaction equation

HRID 540414 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([O:12][C:13]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[CH2:16][NH:15][CH2:14]1)[CH2:9][CH2:10][CH3:11].C(OC(N1CCC1)=O)(C)(C)C>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([O:12][C:13]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])[CH2:14][NH:15][CH2:16]1)[CH2:9][CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 669890303-Butoxy-3-o-tolyl-azetidine 1-(tert-butoxycarbonyl)azetidine

Product 1

HCID 669880653-Butoxy-3-o-tolylazetidine trifluoroacetateYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 ml of trifluoroacetic acid is added to a solution containing 500 mg (1.65 mmol) of 3-butoxy-3-o-tolyl-azetidine-1-(tert-butoxycarbonyl)azetidine dissolved in 5 ml of dichloromethane. The reaction medium is stirred at ambient temperature for 3 hours and then concentrated. The crude product obtained is purified by silica gel chromatography (eluent: 90/10 dichloromethane/methanol). 400 mg in the form of a pale yellow powder are obtained with a yield of 76%.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-be9536a225de418eb18f0d60ea52d3c0
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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