Diisopropylethylamine → HCID 178453955, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of trans (4-hydroxymethyl-cyclohexyl)-carbamic acid tert-butyl ester (10.0 g, 43.7 mmol) in DCM (225 mL) was treated with dimethylsulfoxide (DMSO) (75 mL) and then cooled to 0° C. Diisopropylethylamine (30.4 mL, 0.17 mol) was added followed by dropwise addition of a fine suspension of sulphur trioxide pyridine complex (27.8 g, 0.17 mol) in DMSO (75 mL). The mixture was stirred at ambient temperature for 10 minutes and then diluted with diethyl ether and 1N aqueous hydrochloric acid with cooling in an ice bath. The phases were separated and the aqueous layer was extracted with ether (×2) and the combined organic phases were washed with 1N aqueous hydrochloric acid, and brine, dried with sodium sulfate and concentrated under vacuum. Trituration with pentane gave 9.36 g (94%) of trans (4-formyl-cyclohexyl)-carbamic acid tert-butyl ester as a white solid which was used without further purification. 1H NMR (400 MHz, CDCl3) δ: 9.62 (d, 1H), 4.40 (br s, 1H), 3.51-3.28 (m, 1H), 2.20-1.99 (m, 4H), 1.44 (s, 9H), 1.38 (m, 2H), 1.16 (m, 2H).

Provenance & Evidence