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Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → methyl 7-(N-benzyloxycarbonylamino)-3-hydroxy-2-phenylheptanoate

HRID 2392928
ノート
印刷プレビュー

反応式

HRID 2392928 の反応式
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[O:28])[CH:17]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn](Cl)(Cl)(Cl)Cl.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.[H][H]>CO>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([OH:28])[CH:17]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-2 回HCID 24287Tin tetrachlorideHCID 11036381methyl 7-(N-benzyloxycarbonylamino)-3-oxo-2-phenylheptanoateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 18980747methyl 7-(N-benzyloxycarbonylamino)-3-hydroxy-2-phenylheptanoate収率 87.4%

試薬・触媒・溶媒

1
HCID 887Methanol溶媒

実験手順

22.6 g (58.8 mmol) of methyl 7-(N-benzyloxycarbonylamino)-3-oxo-2-phenylheptanoate, 435 mg (0.39 mmol) of [RuI(p-cymene)(S)-BINAP]I, 72 mg (0.39 mmol) of tin chloride and 364 mg (1.56 mol) of camphor-10-sulfonic acid (hereinafter referred to as "CSA") were placed in a 500 ml autoclave. After air in the autoclave was replaced with nitrogen, 160 ml of methanol was added to the mixture. The nitrogen in the autoclave was replaced with hydrogen and then the mixed solution was reacted at 80° C. under a hydrogen pressure of 80 kg/cm2 for 40 hours. After the completion of the reaction was confirmed by means of HPLC, the reaction solution was concentrated under reduced pressure. The residue was then purified by means of SGIC (eluent: hexane/ethylacetate=2/1 by volume) to prepare the target compound as a colorless oil in an amount of 37.4 g at a yield of 87.4%. The products were analyzed using HPLC. As a result, the rate of the syn-form to the anti-form was 76.3:23.7 and the optical purity of each of the forms was 95.6% ee and 97.8% ee respectively. The analytical results on the target compound are given below.

後処理

  1. additionwas added to the mixture
  2. customthe mixed solution was reacted at 80° C. under a hydrogen pressure of 80 kg/cm2 for 40 hours
  3. concentrationthe reaction solution was concentrated under reduced pressure
  4. customThe residue was then purified by means of SGIC (eluent: hexane/ethylacetate=2/1 by volume)
  5. customto prepare the target compound as a colorless oil in an amount of 37.4 g at a yield of 87.4%
  6. customThe analytical results on the target compound

出典と根拠

ORDレコード
ord-d22d4d91df2d441ab7169068ba1afe76
出典データセット
uspto-grants-1998_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05801271

反応ノート

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