반응 #43641

반응 방정식

Water

Phenylmethyl (3R,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-hydroxy-1-piperidinecarboxylate

sodium hydroxide

dimethyl sulphate

cis-4-tertbutoxycarbonylamino-3-hydroxy-piperidine-1-carboxylic acid benzyl ester

→

title compound

Phenylmethyl (3R,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-(methyloxy)-1-piperidinecarboxylate

용매

THF

반응 조건

후처리

1. 1
   추출the product was extracted with ethyl acetate (150 ml)
2. 2
   기타The organic phase was separated
3. 3
   기타dried
4. 4
   여과Filtration and evaporation to dryness

실험 절차

Phenylmethyl (3R,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-3-hydroxy-1-piperidinecarboxylate (for a synthesis, see WO2004058144, Example 5 (b) cis-4-tertbutoxycarbonylamino-3-hydroxy-piperidine-1-carboxylic acid benzyl ester, Enantiomer 1) (2.2 g, 6.28 mmol) in THF (12 ml) was treated with 50% sodium hydroxide solution (12 ml), benzyltriethylammonium chloride (0.04 g) and dimethyl sulphate (1.31 g, 10.43 mmol) and stirred at RT for 60 hours. Water (100 ml) was added and the product was extracted with ethyl acetate (150 ml). The organic phase was separated and dried. Filtration and evaporation to dryness gave the title compound (2.2 g).

출처