2,2,2-Trifluoroethanol → (R)-2-amino-1-(3,3-difluoro-azetidin-1-yl)-propan-1-one

HRID 245822Notes

Reaction equation

HRID 245822 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH3:17])[C:9]([N:11]1[CH2:14][C:13]([F:16])([F:15])[CH2:12]1)=[O:10])(C)(C)C.FC(F)(F)CO>>[NH2:7][C@H:8]([CH3:17])[C:9]([N:11]1[CH2:14][C:13]([F:16])([F:15])[CH2:12]1)=[O:10]

Participants

3

Reactant 2

HCID 64092,2,2-TrifluoroethanolHCID 71279993[(R)-2-(3,3-difluoro-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 86677900(R)-2-amino-1-(3,3-difluoro-azetidin-1-yl)-propan-1-oneYield 97.1%

Conditions

Temperature
150 °C

Procedure

A 5 ml microwave vial was charged with [(R)-2-(3,3-difluoro-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester (170 mg, 0.64 mmol) and 2,2,2-trifluoroethanol (2.4 ml, 32.9 mmol). The vial was flushed with argon, sealed and heated at 150° C. under microwave irradiation for 3 h. The reaction mixture was concentrated to afford 102 mg (97%) of (R)-2-amino-1-(3,3-difluoro-azetidin-1-yl)-propan-1-one as a brown oil which was used without further purification.

Workup

  1. customThe vial was flushed with argon
  2. customsealed
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-3be26b08e6964524a813bf5c3beabb8c
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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