tert-butyl N-(2-oxoethyl)carbamate → HCID 86612293, compound

Participants

Reaction Steps

Stir a solution of N-((1R,3S)-5-methoxy-6-methyl-3-(4-piperidinyl)-1-isochromanyl-methyl)formamide (4.0 g, 12.5 mmole) in dichloroethane (110 mL) and add sodium triacetoxyborohydride (4.0 g, 18.8 mmole). Dissolve t-butyl N-(2-oxoethyl)-carbamate (1.0 g, 6.3 mmole) in dichloroethane (20 mL) and add it to the reaction mixture. After 6 hours add another 6.3 mmole of t-butyl N-(2-oxoethyl)-carbamate in dichloroethane. After another 42 hours adjust the pH of the reaction mixture to about 14 with 50% NaOH and extract with dichloromethane. Wash the combined extracts with water and dry over Mg2SO4. Purify the crude product on a 33 g silica gel column (eluting with ammonium hydroxide:methanol:ethyl acetate 1:1:98). Collect the appropriate fractions and concentrate to obtain the title compound. CIMS 462, tR (min)=0.46.

Provenance & Evidence