1-(5-Trifluoromethyl-pyridin-2-yl)-piperazine → (2S)-2-{4-[5-(Trifluoromethyl)pyridin-2-yl]piperazin-1-yl}propanoic acid

HRID 2276945Notes

Reaction equation

[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:7][CH:8]=1.Br[C@H:18]([CH3:22])[C:19]([OH:21])=[O:20]>C(Cl)Cl>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C@@H:18]([CH3:22])[C:19]([OH:21])=[O:20])[CH2:13][CH2:14]2)=[N:7][CH:8]=1

Participants

Conditions

Temperature: 35 °C

Procedure

A solution of 1-(5-trifluoromethyl-pyridin-2-yl)-piperazine (2.77 g, 11.99 mmoles) in DCM (42 mL) and TEA (4.2 mL) was treated with (2R)-2-bromo-propionic acid (1.19 mL, 13.2 mmoles) and stirred overnight at 35° C. The DCM was removed under reduced pressure to provide crude title compound as a yellowish solid that was used in the next step. MS (APCI+) m/z 304 (M+H)+.

Workup

customThe DCM was removed under reduced pressure

Sources & evidence

ORD record: ord-6757415383d549f2822d4a4f06f3a140
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133145B2

Reaction notes

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