Water → HCID 178444563, compound
Reaction equation
[CH2:1](S(C1N(C2C=CC=CC=2)N=NN=1)(=O)=O)[CH2:2][CH2:3][CH3:4].[K].C[Si](C)(C)N[Si](C)(C)C.[CH:29]([C@@H:31]1[CH2:36][CH2:35][C@H:34]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:33][CH2:32]1)=O.O>COCCOC>[CH:29](/[C@@H:31]1[CH2:36][CH2:35][C@H:34]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:33][CH2:32]1)=[CH:1]\[CH2:2][CH2:3][CH3:4]Participants
Conditions
- Temperature
- 25 °C
Procedure
To a mixture of 5-butylsulfonyl-1-phenyl-1H-tetrazole (3.54 g) and anhydrous ethylene glycol dimethyl ether (60 ml) at −60° C. was added 0.5 M hexamethyldisilazane potassium solution (in toluene, 26.6 ml), and the mixture was stirred for 20 minutes. Under the same condition, a solution of t-butyl cis-4-formylcyclohexylcarbamate (3.02 g) in anhydrous ethylene glycol dimethyl ether (15 ml) was added to the mixture. And the reaction mixture was gradually warmed to 25° C. and stirred overnight. To the reaction mixture was added water, and the mixture was stirred for 1 hour, then extracted with diethyl ether, and the organic layer was washed with brine, dried over sodium sulfate, and then the solvent was removed in vacuo. The residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate) to give 2.38 g of t-butyl cis-{4-[(E)-1-pentenyl]cyclohexyl}carbamate.
Workup
- stirringstirred overnight
- stirringthe mixture was stirred for 1 hour
- extractionextracted with diethyl ether
- washthe organic layer was washed with brine
- dry with materialdried over sodium sulfate
- customthe solvent was removed in vacuo
- customThe residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate)
Sources & evidence
- ORD record
- ord-c7bd9161aa24401eb5079031fbaee68c
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767854B2
Reaction notes
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