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Sodium borohydride → (R)-N-naphthalene-2-sulfonyl (3-hydroxy-cyclohepty)glycine ethyl ester

HRID 77330
ノート
印刷プレビュー

反応式

HRID 77330 の反応式
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([C@@H:20]1[CH2:26][CH2:25][CH2:24][CH2:23][C:22](=[O:27])[CH2:21]1)[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(=[O:9])=[O:8])[CH3:2].[BH4-].[Na+]>O1CCCC1CCO>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][N:6]([C@@H:20]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]([OH:27])[CH2:21]1)[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(=[O:8])=[O:9])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 86653278(R)-N-naphthalene-2-sulfonyl (3-oxo-cyclohepty)glycine ethyl ester

生成物 1

HCID 86653277(R)-N-naphthalene-2-sulfonyl (3-hydroxy-cyclohepty)glycine ethyl ester収率 85%

試薬・触媒・溶媒 1

HCID 119895722-(Oxolan-2-yl)ethan-1-ol溶媒

反応条件

温度
0 °C

実験手順

To a solution of (R)—N-naphthalene-2-sulfonyl (3-oxo-cyclohepty)glycine ethyl ester (1.05 g, 2.61 mmol) in tetrahydrofuran-ethanol (20 mL, 1:1) at 0° C. is added sodium borohydride (0.147 g, 3.88 mmol) and the reaction is stirred at 0° C. for 1 hour. The reaction was quenched at 0° C. with citric acid (10% aqueous), and the solvents were removed in vacuo. The residue was dissolved in water and extracted three times with ethyl acetate. The combined organic extracts were washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by column chromatography (50% hexanes-ethyl acetate) to afford the title compound as a white solid (0.90 g, 85% yield). LCMS (m/z): 406.14 (M+1), 404.13 (M−1).

後処理

  1. customThe reaction was quenched at 0° C. with citric acid (10% aqueous)
  2. customthe solvents were removed in vacuo
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography (50% hexanes-ethyl acetate)

出典と根拠

ORDレコード
ord-48ea1697e4ac4b93ba100314d0fe3485
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08841291B2

反応ノート

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