2-Butyn-1-yl chloroformate → but-2-ynyl 3-[4-[(3aS,7aS)-2-oxo-3a,4,5,6,7,7a-hexahydro-3H-benzimidazol-1-yl]-1-piperidyl]-3-methyl-pyrrolidine-1-carboxylate

HRID 1642503Notes

Reaction equation

HRID 1642503 reaction equation
[CH3:1][C:2]1([N:7]2[CH2:12][CH2:11][CH:10]([N:13]3[C@H:17]4[CH2:18][CH2:19][CH2:20][CH2:21][C@@H:16]4[NH:15][C:14]3=[O:22])[CH2:9][CH2:8]2)[CH2:6][CH2:5][NH:4][CH2:3]1.Cl[C:24]([O:26][CH2:27][C:28]#[C:29][CH3:30])=[O:25]>>[O:22]=[C:14]1[N:13]([CH:10]2[CH2:11][CH2:12][N:7]([C:2]3([CH3:1])[CH2:6][CH2:5][N:4]([C:24]([O:26][CH2:27][C:28]#[C:29][CH3:30])=[O:25])[CH2:3]3)[CH2:8][CH2:9]2)[C@H:17]2[CH2:18][CH2:19][CH2:20][CH2:21][C@@H:16]2[NH:15]1

Participants

3

Reactant 2

HCID 41316692-Butyn-1-yl chloroformateHCID 57619793(3aS,7aS)-1-[1-(3-methylpyrrolidin-3-yl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-3H-benzoimidazol-2-one

Product 1

HCID 25221450but-2-ynyl 3-[4-[(3aS,7aS)-2-oxo-3a,4,5,6,7,7a-hexahydro-3H-benzimidazol-1-yl]-1-piperidyl]-3-methyl-pyrrolidine-1-carboxylateYield 33.9%

Procedure

Following the procedure used in example 16 and starting from (3aS,7aS)-3-[1-(3-methylpyrrolidin-3-yl)-4-piperidyl]-3a,4,5,6,7,7a-hexahydro-1H-benzimidazol-2-one (HCl salt, 0.6 g, 1.75 mmol) and but-2-ynyl chloroformate (0.218 mL, 1.92 mmol), the title compound (0.239 g, 33.9%) was obtained after purification by preparative LC/MS (high pH) as a mixture of diastereomers. MS (M+1): 403.3

Sources & evidence

ORD record
ord-28fa545b4ff6403081d920b300f3a48a
Source dataset
uspto-grants-2012_02
Patent number
US08119661B2

Reaction notes

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