Methyl 2,4-dibromobutanoate → Methyl 1-(1-(2,2,2-trifluoroethyl)piperidin-4-yl)azetidine-2-carboxylate

HRID 2403160Notes

Reaction equation

HRID 2403160 reaction equation
Br[CH:2]([CH2:7][CH2:8]Br)[C:3]([O:5][CH3:6])=[O:4].Cl.[F:11][C:12]([F:22])([F:21])[CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([NH2:20])[CH2:16][CH2:15]1>>[F:22][C:12]([F:11])([F:21])[CH2:13][N:14]1[CH2:19][CH2:18][CH:17]([N:20]2[CH2:8][CH2:7][CH:2]2[C:3]([O:5][CH3:6])=[O:4])[CH2:16][CH2:15]1

Participants

3

Reactant 2

HCID 296716Methyl 2,4-dibromobutanoateHCID 178400021-(2,2,2-Trifluoroethyl)piperidin-4-amine hydrochloride

Product 1

HCID 86692753Methyl 1-(1-(2,2,2-trifluoroethyl)piperidin-4-yl)azetidine-2-carboxylateYield 8%

Procedure

The reaction of methyl 2,4-dibromobutanoate 17 with 1-(2,2,2-trifluoroethyl)piperidin-4-amine hydrochloride 18G yielded methyl 1-(1-(2,2,2-trifluoroethyl)piperidin-4-yl)azetidine-2-carboxylate as a light brown solid (8%). MS ISP (m/e): 281.1 (100) [(M+H)]+.

Sources & evidence

ORD record
ord-959c923e8a75466795a5530835bd4c99
Source dataset
uspto-grants-2014_08
Patent number
US08802665B2

Reaction notes

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