Potassium Carbonate → tert-Butyl methylcarbamate

Temperature

100 °C

0.700 g (1.42 mmol) of 3-benzyloxypropyl)triphenylphosphonium bromide, 0.305 g (1.18 mmol) of trans-(4-formyl-cyclohexylmethyl)-methyl-carbamic acid tert-butyl ester (example 1.2) and 0.662 g of finely milled potassium carbonate were suspended in 10.0 ml of 2-methyl-2-butanol and the reaction mixture intensively stirred at 100° C. for 2 hours. It was then evaporated, poured into 50 ml of an ice/water mixture and extracted 3 times with 50 ml of ethylacetate. The combined ethylacetate phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 95:5 v/v mixture of dichloromethane and ether as the eluent giving 0.364 g (78.6%) trans-[4-(4-benzyloxy-[E/Z 1:9]but-1-enyl)-cyclohexylmethyl]-methyl-carbamic acid tert-butyl ester as colorless viscous oil, MS: 331 [M−C4H8)+].

1. customIt was then evaporated
2. additionpoured into 50 ml of an ice/water mixture
3. extractionextracted 3 times with 50 ml of ethylacetate
4. dry with materialThe combined ethylacetate phases were dried over magnesium sulfate
5. customevaporated under reduced pressure
6. customThe residue formed
7. customwas chromatographed on silica gel with a 95:5 v/v mixture of dichloromethane and ether as the eluent

ORD record

ord-cfbefdbf73034471aa7eef87dd6a53d3

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06953806B2