Tributylstannane → 2-Benzyloxycarbonylamino-3-(1-methylcyclopentyl)propionic acid methyl ester

HRID 17003Notes

Reaction equation

HRID 17003 reaction equation
[CH2:1]([SnH](CCCC)CCCC)CCC.[CH2:14]=[C:15]([NH:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])[C:16]([OH:18])=[O:17].[CH3:30][C:31]1(Br)[CH2:35][CH2:34][CH2:33][CH2:32]1.CC(N=NC(C#N)(C)C)(C#N)C>C1C=CC=CC=1>[CH3:1][O:17][C:16](=[O:18])[CH:15]([NH:19][C:20]([O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:21])[CH2:14][C:31]1([CH3:30])[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 4674477Z-dehydro-Ala-OHHCID 129395091-Bromo-1-methylcyclopentane

Product 1

HCID 673914702-Benzyloxycarbonylamino-3-(1-methylcyclopentyl)propionic acid methyl esterYield 38.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Tributyltin hydride (37.8 g, 130 mmol) was added at reflux to a 500 mL of flask charged with benzene (200 mL) was added Z-dehydro-Ala-OH (15 g, 64 mmol), 1-methylcyclopentanyl-bromide (20.5 g) and AIBN (1.9 g). After 2 h, the solvent was removed and the residue was purified by column chromatograph to yield 2-benzyloxycarbonylamino-3-(1-methyl-cyclopentyl)-propionic acid methyl ester (7.9 g).

Workup

  1. temperatureat reflux to a 500 mL of flask
  2. customthe solvent was removed
  3. customthe residue was purified by column chromatograph

Sources & evidence

ORD record
ord-ac7647b5c5fd44d3b5ff6aa04d73c5dc
Source dataset
uspto-grants-2010_06
Patent number
US07737300B2

Reaction notes

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