Imidazole → benzyl (1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-2-((Z)-prop-1-enyl)cyclohexylcarbamate

HRID 1171523Notes

Reaction equation

[OH:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:4](/[CH:19]=[CH:20]\[CH3:21])[CH2:3]1.N1C=CN=C1.[C:27]([Si:31](Cl)([CH3:33])[CH3:32])([CH3:30])([CH3:29])[CH3:28]>C(Cl)Cl>[Si:31]([O:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C@H:4](/[CH:19]=[CH:20]\[CH3:21])[CH2:3]1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:33])[CH3:32]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of benzyl (1S,2S,4R)-4-hydroxy-2-((Z)-prop-1-enyl)cyclohexylcarbamate (6.0 g, 20.7 mmol) in methylene chloride (60 mL) was treated with imidazole (2.1 g) and cooled to 0° C. The resultant solution was charged with tert-butylchlorodimethylsilane (3.4 g, 22.8 mmol) and then stirred for 18 h at 30° C. before being quenched with water. The organic phase was separated, and the aqueous phase was extracted with methylene chloride. The combined organic phases were washed with brine, dried, filtered, and concentrated in vacuo. The residue was purified by flash chromatography to afford benzyl (1S,2S,4R)-4-(tert-butyldimethylsilyloxy)-2-((Z)-prop-1-enyl)cyclohexylcarbamate (6.0 g). MS found: (M+H)+=404.

Workup

custombefore being quenched with water
customThe organic phase was separated
extractionthe aqueous phase was extracted with methylene chloride
washThe combined organic phases were washed with brine
customdried
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-c68589e063724aba82e8601c9b358fa5
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07829571B2

Reaction notes

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