Triethylamine → (S)-3-((R)-2-(3-chlorophenyl)morpholino)-1,1,1-trifluoropropan-2-ol

HRID 530595Notes

Reaction equation

Cl.[Cl:2][C:3]1[CH:4]=[C:5]([C@H:9]2[O:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.C(N(CC)CC)C.[F:22][C:23]([F:28])([F:27])[C@@H:24]1[CH2:26][O:25]1>C(#N)C>[Cl:2][C:3]1[CH:4]=[C:5]([C@@H:9]2[CH2:10][N:11]([CH2:26][C@H:24]([OH:25])[C:23]([F:28])([F:27])[F:22])[CH2:12][CH2:13][O:14]2)[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (R)-2-(3-chloro-phenyl)-morpholine hydrochloride (45 mg, 192 μmol) and triethylamine (134 μL, 961 μmole) in 4 mL of acetonitrile was added (S)-2-(trifluoromethyl)oxirane (43.1 mg, 384 μmol). The mixture was stirred at 50° C. for 3 h, followed by evaporation in vacuo to afford (S)-3-((R)-2-(3-chlorophenyl)morpholino)-1,1,1-trifluoropropan-2-ol (59.5 mg), which was used directly for next step.

Workup

customfollowed by evaporation in vacuo

Sources & evidence

ORD record: ord-7c6fd793f5554079818357ab2262f362
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353096B2

Reaction notes

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