(2S)-2-(Trifluoromethyl)oxirane → (S)-3-((R)-2-(4-chloro-3-fluorophenyl)morpholino)-1,1,1-trifluoropropan-2-ol

HRID 530592Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[O:13][CH2:12][CH2:11][NH:10][CH2:9]2)=[CH:4][C:3]=1[F:14].[F:15][C:16]([F:21])([F:20])[C@@H:17]1[CH2:19][O:18]1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:9][N:10]([CH2:19][C@H:17]([OH:18])[C:16]([F:21])([F:20])[F:15])[CH2:11][CH2:12][O:13]2)=[CH:4][C:3]=1[F:14]

Participants

Conditions

Temperature: 60 °C

Procedure

(R)-2-(4-chloro-3-fluorophenyl)morpholine (230 mg, 1.07 mmol) was mixed with (S)-2-(trifluoromethyl)oxirane (180 mg, 1.6 mmol) in 1 mL of dichloromethane in a tube. The tube was sealed and stirred at 60° C. overnight. The solution was evaporated to dryness to afford (S)-3-((R)-2-(4-chloro-3-fluorophenyl)morpholino)-1,1,1-trifluoropropan-2-ol as an oil (340 mg), which was used as is in the next step. (M+H)+=328 m/e.

Workup

customThe tube was sealed
customThe solution was evaporated to dryness

Sources & evidence

ORD record: ord-a045f40b04be4e31b12bca27ab3f46dd
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353096B2

Reaction notes

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