HCID 57296559, 화합물 → benzyl N-[(1S,3R)-rel-3-hydroxycyclopentyl]carbamate

HRID 1086800노트

반응식

HRID 1086800 반응식
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[N:3]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[O:2]2>C(O)(=O)C.O.[Zn]>[OH:2][C@@H:1]1[CH2:6][CH2:5][C@H:4]([NH:3][C:8](=[O:9])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7]1

참가 물질

5

반응물 1

HCID 57296559HCID 57296559, 화합물

생성물 1

HCID 86331931benzyl N-[(1S,3R)-rel-3-hydroxycyclopentyl]carbamate수율 23.8%

시약·촉매·용매 3

HCID 23994Zinc촉매2회HCID 176Acetic Acid용매3회HCID 962Water용매

실험 절차

A solution 3-aza-2-oxabicyclo[2.2.1]heptane-3-carboxylic acid, (phenylmethyl) ester (0.5 g) in glacial acetic acid (0.5 ml) was added to a stirred suspension of powdered zinc (0.35 g) in a mixture of acetic acid and water (1:1; 4 ml), and the mixture was stirred at 60° for 7.5 h. Additional zinc powder (0.14 g) and acetic acid (1 ml) were added and stirring was continued for a further 16.5 h. After cooling to room temperature, the mixture was filtered and the excess of zinc washed with 2M hydrochloric acid (20 ml). The combined filtrate and washings were neutralised with 8% sodium carbonate and extracted into ethyl acetate (3×30 ml). The combined organic extracts were washed with brine (30 ml), dried and concentrated in vacuo. Purification by FCC eluting with ethyl acetate: cyclohexane (1:1) gave an oil (120 mg) which solidified upon standing and was recrystallised from cyclohexane to give the title compound (70 mg), m.p. 62°-63°.

후처리

  1. stirringstirring
  2. waitwas continued for a further 16.5 h
  3. filtrationthe mixture was filtered
  4. washthe excess of zinc washed with 2M hydrochloric acid (20 ml)
  5. extractionextracted into ethyl acetate (3×30 ml)
  6. washThe combined organic extracts were washed with brine (30 ml)
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customPurification by FCC
  10. washeluting with ethyl acetate: cyclohexane (1:1)

출처 및 근거

ORD 기록
ord-6e2643c00103427dace5973aeb37e87a
출처 데이터셋
uspto-grants-1991_07
특허 번호
US05032583

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