2,2,2-Trifluoroethanol → (R)-3-Amino-1-methylpiperidin-2-one

HRID 446944Notes

Reaction equation

HRID 446944 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([NH:8]C(=O)OC(C)(C)C)[C:3]1=[O:16].FC(F)(F)CO>>[NH2:8][C@@H:4]1[CH2:5][CH2:6][CH2:7][N:2]([CH3:1])[C:3]1=[O:16]

Participants

3

Reactant 2

HCID 64092,2,2-TrifluoroethanolHCID 67388684(R)-tert-Butyl(1-methyl-2-oxopiperidin-3-yl)carbamate

Product 1

HCID 57516592(R)-3-Amino-1-methylpiperidin-2-oneYield 69%

Procedure

A solution of (R)-tert-butyl 1-methyl-2-oxopiperidin-3-ylcarbamate (310 mg, 1.36 mmol) in 2,2,2-trifluoroethanol (4.95 mL, 67.9 mmol) was heated at 150° C. for 3 h under microwave assisted conditions. The solvent was evaporated to dryness and the crude residue was purified by SiO2 chromatography (11 g, CH2Cl2/MeOH/NH4OH, 100:0:0 to 94:5.7:0.3) to give 120 mg (69%) of (R)-3-amino-1-methyl-piperidin-2-one as a light yellow oil.

Workup

  1. customThe solvent was evaporated to dryness
  2. customthe crude residue was purified by SiO2 chromatography (11 g, CH2Cl2/MeOH/NH4OH, 100:0:0 to 94:5.7:0.3)

Sources & evidence

ORD record
ord-1e3f9b196c9340afaaad93cc8a697017
Source dataset
uspto-grants-2013_07
Patent number
US08481541B2

Reaction notes

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