Trifluoroacetic acid → 3-Azetidinol, 3-acetate, 2,2,2-trifluoroacetate (1:1)

HRID 1778408Notes

Reaction equation

HRID 1778408 reaction equation
[C:1]([O:4][CH:5]1[CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6]1)(=[O:3])[CH3:2].[C:16]([OH:22])([C:18]([F:21])([F:20])[F:19])=[O:17]>C(Cl)Cl>[F:19][C:18]([F:21])([F:20])[C:16]([OH:22])=[O:17].[NH:7]1[CH2:8][CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH2:6]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58334039Tert-butyl 3-acetoxyazetidine-1-carboxylate2×

Product 1

HCID 666857643-Azetidinol, 3-acetate, 2,2,2-trifluoroacetate (1:1)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-acetoxyazetidine-1-carboxylate (Intermediate 95, 0.914 g) in DCM (5 mL) was added TFA (5 mL) and the mixture was stirred at room temperature for 30 minutes. The resultant mixture was concentrated in vacuo and azeotroped with toluene and diethyl ether to give acetic acid azetidin-3-yl ester trifluoroacetate salt (1.40 g) as a clear oil.

Workup

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. customazeotroped with toluene and diethyl ether

Sources & evidence

ORD record
ord-efa45ac8e05a41dbac28ca9a9c221eb9
Source dataset
uspto-grants-2016_02
Patent number
US09266896B2

Reaction notes

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