Tributylstannane → Methyl 2-(benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propanoate

HRID 451785Notes

Reaction equation

Br[C:2]1([CH3:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C([SnH](CCCC)CCCC)CCC.[CH2:22]([O:29][C:30]([NH:32][C:33](=[CH2:38])[C:34]([O:36][CH3:37])=[O:35])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N(C(C)(C)C#N)=NC(C)(C)C#N>C1C=CC=CC=1>[CH2:22]([O:29][C:30]([NH:32][CH:33]([CH2:38][C:2]1([CH3:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)[C:34]([O:36][CH3:37])=[O:35])=[O:31])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 1-bromo-1-methylcyclohexane (7.200 g, 3.0 equiv), tributyltin hydride (8 mL, 2.2 equiv), methyl 2-(benzyloxycarbonylamino)acrylate (3.120 g, 13.26 mmol, 1.0 equiv), and 2,2′-azobisisobutyronitrile (0.370 g, 0.17 equiv) in benzene (30 mL) was heated at 100° C. for 6 h. After the reaction mixture was evaporated under reduced pressure, the crude methyl 2-(benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propanoate was used directly in the next step without further purification. MS ESI +ve m/z 356 (M+Na).

Workup

customAfter the reaction mixture was evaporated under reduced pressure
customthe crude methyl 2-(benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propanoate was used directly in the next step without further purification

Sources & evidence

ORD record: ord-6236388c73a9446e86fe57190f3c8112
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487108B2

Reaction notes

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