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

HRID 1086800ノート

反応式

HRID 1086800 の反応式
[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

参加物

5

反応物 1

HCID 57296559HCID 57296559、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒2 回HCID 176Acetic Acid溶媒3 回HCID 962Water溶媒

実験手順

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°.

後処理

  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)

出典と根拠

ORDレコード
ord-6e2643c00103427dace5973aeb37e87a
出典データセット
uspto-grants-1991_07
特許番号
US05032583

反応ノート

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