Hydrazine → 3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ol

HRID 338833Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]([C@H:8]([N:13]2[CH2:17][CH2:16][C:15]([CH3:19])([OH:18])[CH2:14]2)[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.[NH2:20][NH2:21]>C(O)(CC)C>[CH3:19][C:15]1([OH:18])[CH2:16][CH2:17][N:13]([C@@H:8]([C:5]2[CH:6]=[N:7][C:2]([NH:20][NH2:21])=[CH:3][CH:4]=2)[C:9]([F:12])([F:11])[F:10])[CH2:14]1

Participants

Conditions

Temperature: 125 °C

Procedure

To a solution of Diastereomer 1 of 1-((S)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl)-3-methylpyrrolidin-3-ol (0.550 g, 1.866 mmol) in sec-butanol (10 mL) was added hydrazine (0.8786 mL, 27.99 mmol) and stirred at 125° C. overnight. The reaction was concentrated from methanol (3×30 mL) to give Diastereomer 1 of 3-methyl-1-((S)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ol (0.580 g, 1.998 mmol, 107.1% yield).

Workup

concentrationThe reaction was concentrated from methanol (3×30 mL)

Sources & evidence

ORD record: ord-ff2ff5ab3b6f469fa73436b1137f9591
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889704B2

Reaction notes

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