Trifluoroacetic acid → 3-methylazetidin-3-ol: trifluoroacetic acid

HRID 1898565Notes

Reaction equation

HRID 1898565 reaction equation
C(OC([N:8]1[CH2:11][C:10]([OH:13])([CH3:12])[CH2:9]1)=O)(C)(C)C.[F:14][C:15]([F:20])([F:19])[C:16]([OH:18])=[O:17]>ClCCl>[F:14][C:15]([F:20])([F:19])[C:16]([OH:18])=[O:17].[CH3:12][C:10]1([OH:13])[CH2:11][NH:8][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54751705tert-Butyl 3-hydroxy-3-methylazetidine-1-carboxylate

Product 1

HCID 668475833-methylazetidin-3-ol: trifluoroacetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a round-bottomed flask, 3-hydroxy-3-methyl-azetidine-1-carboxylic acid tert-butyl ester (0.40 g, 2.13 mmol) was dissolved in dichloromethane (20 mL). The colorless solution was cooled to 0° C. and trifluoroacetic acid (6.5 ml) was slowly added. After the addition was complete, the ice bath was removed and the reaction mixture was stirred at room temperature for 1.5 h. The reaction mixture was concentrated to afford 3-methyl-azetidin-3-ol trifluoroacetate as light brown oil which was used without further purification.

Workup

  1. additionAfter the addition
  2. customthe ice bath was removed
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-41bb4c88461f4357bb4ed0a776447c25
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

Loading…