Potassium Bicarbonate → tert-Butyl ((1S,3S)-3-hydroxycyclopentyl)carbamate

HRID 582533노트

반응식

HRID 582533 반응식
[CH3:1][C:2]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([O:13]C=O)[CH2:9]1)([CH3:4])[CH3:3].C(=O)([O-])O.[K+]>CO.O.C(OCC)(=O)C>[CH3:4][C:2]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)([CH3:1])[CH3:3]

참가 물질

6

반응물 2

HCID 516893Potassium BicarbonateHCID 86754023(1S,3S)-3-[(tert-Butoxycarbonyl)amino]cyclopentyl formate

생성물 1

HCID 21637082tert-Butyl ((1S,3S)-3-hydroxycyclopentyl)carbamate수율 52.5%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of (1S-trans)-[3-(formyloxy)cyclopentyl]carbamic acid 1,1-dimethylethyl ester (0.081 g, 0.35 mmol) in methanol (3 ml) was treated with a slurry of potassium hydrogen carbonate (0.707 g, 7.06 mmol) in water (1.5 ml) and stirred at room temperature for 2h. The mixture was then diluted with water (20 ml) and ethyl acetate (20 ml) and the aqueous phase was extracted with ethyl acetate (2×20 ml). The combined organic phase was dried (MgSO4) and evaporated to leave a solid which was purified by column chromatography on flash silica eluting with 30-40% ethyl acetate in cyclohexane to give the title compound (0.037 g) from diisopropyl ether m.p. 83-85° C., [α]D 0.0° (CHCl3 c=0.55%).

후처리

  1. extractionthe aqueous phase was extracted with ethyl acetate (2×20 ml)
  2. dry with materialThe combined organic phase was dried (MgSO4)
  3. customevaporated
  4. customto leave a solid which
  5. customwas purified by column chromatography on flash silica eluting with 30-40% ethyl acetate in cyclohexane

출처 및 근거

ORD 기록
ord-5c6b4d35a75f46c08faf4e9123193d33
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05925624

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