2-Butene, 1-bromo-3-methyl- → {(S)-1-[(2S,4R)-4-(3-Methyl-but-2-enyl)-5-oxo-tetrahydro-furan-2-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

HRID 1373096Notes

Reaction equation

HRID 1373096 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]([CH:16]1[CH2:20][CH:19]([CH3:21])[C:18](=[O:22])[O:17]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].BrC[CH:26]=[C:27]([CH3:29])[CH3:28]>>[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]([C@@H:16]1[CH2:20][C@@H:19]([CH2:21][CH:26]=[C:27]([CH3:29])[CH3:28])[C:18](=[O:22])[O:17]1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 700922-Butene, 1-bromo-3-methyl-HCID 57181317[(S)-1-(4-Methyl-5-oxo-tetrahydrofuran-2-yl)-2-phenylethyl]carbamic acid t-butyl ester

Product 1

HCID 12015737{(S)-1-[(2S,4R)-4-(3-Methyl-but-2-enyl)-5-oxo-tetrahydro-furan-2-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl esterYield 84%

Procedure

Prepared analogously to the synthesis of [(S)-1-(4-methyl-5-oxo-tetrahydrofuran-2-yl)-2-phenylethyl]-carbamic acid t-butyl ester in Journal of Organic Chemistry (1986) 51(21), 3921, using 4-bromo-2-methyl-2-butene in place of methyl iodide, to afford D5 in 84% yield.

Sources & evidence

ORD record
ord-2cc425a43fb3411b9072534dd7fc6d67
Source dataset
uspto-grants-2007_01
Patent number
US07160905B2

Reaction notes

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