2,2,2-Trifluoroethanol → HCID 57516615, compound

HRID 1898530Notes

Reaction equation

HRID 1898530 reaction equation
C(OC(=O)[NH:7][C@@H:8]([C:13]([N:15]1[CH2:20][CH2:19][C:18]([OH:27])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)=[O:14])[C:9]([CH3:12])([CH3:11])[CH3:10])(C)(C)C.FC(F)(F)CO>>[NH2:7][C@H:8]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:13]([N:15]1[CH2:20][CH2:19][C:18]([OH:27])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:17][CH2:16]1)=[O:14]

Participants

3

Reactant 2

HCID 64092,2,2-TrifluoroethanolHCID 67386128HCID 67386128, compound

Product 1

HCID 57516615HCID 57516615, compoundYield 128.3%

Conditions

Temperature
150 °C

Procedure

A 5 mL microwave vial was charged with [(R)-1-(4-hydroxy-4-phenyl-piperidine-1-carbonyl)-2,2-dimethyl-propyl]-carbamic acid tert-butyl ester (0.20 g, 0.51 mmol) and 2,2,2-trifluoroethanol (2.6 mL). The vial was flushed with Argon then sealed and heated at 150° C. for 4 h under microwave irradiation. The reaction mixture was concentrated to afford 0.19 g of (R)-2-amino-1-(4-hydroxy-4-phenyl-piperidin-1-yl)-3,3-dimethyl-butan-1-one as light yellow oil which was used without further purification.

Workup

  1. customThe vial was flushed with Argon
  2. customthen sealed
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-3669a8340b0248c58c168e2ee5ac4ce4
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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