Potassium bisulfate → HCID 178486039, compound

HRID 2057314Notes

Reaction equation

[C:1]([O:5][C:6](=[O:19])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]#[C:16][CH2:17][OH:18])[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].COCCO[AlH2-]OCCOC.[Na+].OS([O-])(=O)=O.[K+]>CCOCC>[C:1]([O:5][C:6](=[O:19])[N:7]([C@H:9]1[CH2:10][CH2:11][C@H:12](/[CH:15]=[CH:16]/[CH2:17][OH:18])[CH2:13][CH2:14]1)[CH3:8])([CH3:2])([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 4.5 g (16.8 mmol) of trans-[4-(3-Hydroxy-prop-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 180 ml Et2O was cooled (0° C.) and treated slowly with a solution of 13.46 ml (47.1 mmol) of Red-Al (70% in toluene). The solution was stirred 2 h at RT, cooled (0° C.) and treated again with 1.3 ml (4.7 mmol) of Red-Al (70% in toluene). After 2 h at RT, the reaction was cooled (−50° C.) and hydrolyzed with a suspension of 3 g MgSO4.7H2O, 3 g silica gel in 4 ml aqueous 10% KHSO4. The cooling bath was removed, THF was added, the mixture was filtered. After evaporation, the residue was dissolved in CH2Cl2, dried over Na2SO4 and evaporated to yield 3.59 g (quantitative) of trans-(1E)-[4-(3-Hydroxy-propenyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester, MS: 270 (MH+).

Workup

temperaturecooled (0° C.)
waitAfter 2 h at RT
temperaturethe reaction was cooled (−50° C.)
customThe cooling bath was removed
additionTHF was added
filtrationthe mixture was filtered
customAfter evaporation
dissolutionthe residue was dissolved in CH2Cl2
dry with materialdried over Na2SO4
customevaporated

Sources & evidence

ORD record: ord-57372d43f4784f8382957026f0fe7788
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07335687B2

Reaction notes

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