Triethylamine → HCID 117870991, compound

HRID 530636Notes

Reaction equation

HRID 530636 reaction equation
C(O)(=O)C(O)=O.[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[O:19][CH2:18][CH2:17][NH:16][CH2:15]2)=[CH:10][CH:9]=1.C(N(CC)CC)C.[F:27][C:28]([F:33])([F:32])[C@@H:29]1[CH2:31][O:30]1>C(#N)C>[F:27][C:28]([F:33])([F:32])[C@@H:29]([OH:30])[CH2:31][N:16]1[CH2:17][CH2:18][O:19][CH:14]([C:11]2[CH:10]=[CH:9][C:8]([F:7])=[CH:13][CH:12]=2)[CH2:15]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7171781(2S)-2-(Trifluoromethyl)oxiraneHCID 17749809HCID 17749809, compound

Product 1

HCID 117870991HCID 117870991, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-(4-fluorophenyl)morpholine oxalate (50 mg, 184 μmol) and triethylamine (128 μL, 922 μmole) in 2.5 mL of acetonitrile was added (S)-2-(trifluoromethyl)oxirane (82.6 mg, 737 μmol) at room temperature. The mixture was stirred at this temperature for 4 days. The solution was purified by reverse phase column chromatography (30-100% acetonitrile in water). The desired fractions were pooled and lyophilized to give (2S)-1,1,1-trifluoro-3-(2-(4-fluorophenyl)morpholino)propan-2-ol (39 mg, 73%). Used as is in the next step.

Workup

  1. customThe solution was purified by reverse phase column chromatography (30-100% acetonitrile in water)

Sources & evidence

ORD record
ord-e48f3e109bc44f2ca2d852b3630c84c7
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

Loading…