Tributylstannane → HCID 59201456, compound

HRID 451875Notes

Reaction equation

HRID 451875 reaction equation
Br[C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[CH3:16][O:17][C:18](=[O:32])[C:19]([NH:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])=[CH2:20].CC(N=NC(C#N)(C)C)(C#N)C.[SnH](CCCC)(CCCC)CCCC>C1C=CC=CC=1>[CH2:25]([O:24][C:22]([NH:21][CH:19]([CH2:20][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[C:18]([O:17][CH3:16])=[O:32])=[O:23])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 5948TributylstannaneHCID 6547AzobisisobutyronitrileHCID 3525700Z-Dehydro-Ala-OMeHCID 59201686HCID 59201686, compound

Product 1

HCID 59201456HCID 59201456, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A benzene solution of ((1R*,2R*)-2-bromocyclohexyloxy)(tert-butyl)dimethylsilane (17.8 g, 0.061 mol), 2-benzyloxycarbonylamino-acrylic acid methyl ester (8 g, 0.037 mol), AIBN (1.22 g, 0.019 mol) was heated to reflux. After 5 minutes, n-Bu3SnH (19.8 mL, 0.074 mol) was added. The resulting mixture was then stirred at reflux for 14 hours. Solvent was removed under reduced pressure, the residue was purified by column chromatography to give methyl 2-(benzyloxycarbonylamino)-3-((1S*,2R*)-2-(tert-butyldimethylsilyloxy)cyclohexyl)propanoate (6.5 g, 24%).

Workup

  1. temperatureat reflux for 14 hours
  2. customSolvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e14fbecd83bd4683b1632386b8989676
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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