Borane → [4-Chloro-3-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-5-ethoxy-phenyl]-methanol

HRID 1990865ノート

反応式

HRID 1990865 の反応式
[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH3:13])=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[N:14]1[CH2:19][CH2:18][S:17](=[O:21])(=[O:20])[CH2:16][CH2:15]1.B>>[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH3:13])=[CH:9][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[N:14]1[CH2:15][CH2:16][S:17](=[O:21])(=[O:20])[CH2:18][CH2:19]1

参加物

3

反応物 2

HCID 6331BoraneHCID 686961184-Chloro-3-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-5-ethoxy-benzoic acid

生成物 1

HCID 68694740[4-Chloro-3-(1,1-dioxo-1lambda6-thiomorpholin-4-yl)-5-ethoxy-phenyl]-methanol

実験手順

To a solution of 4-chloro-3-(1,1-dioxo-1λ6-thiomorpholin-4-yl)-5-ethoxy-benzoic acid (0.17 g, 0.51 mmol, 1.0 equiv) was added borane (1.02 mL, 1.02 mmol, 2.0 equiv; 1 M solution in THF) and the reaction mixture stirred at rt overnight. The reaction was quenched by addition of a few drops of methanol, ethyl acetate was added (50 mL) and the organic phase washed with a 1 M solution of NaOH (3×20 mL). The organic phase was dried over MgSO4, the solvent removed by evaporation under reduced pressure and the crude material used in the next step without further purification. Yield: 0.089 g (58%). 1H NMR (300 MHz, CDCl3): δ 1.39 (t, J=7.0 Hz, 3H), 3.13-3.16 (m, 4H), 3.42-3.45 (m, 4H), 4.04 (q, J=7.0 Hz, 2H), 4.56 (s, 2H), 6.64 (br s, 1H), 6.67 (br s, 1H).

後処理

  1. customThe reaction was quenched by addition of a few drops of methanol, ethyl acetate
  2. additionwas added (50 mL)
  3. washthe organic phase washed with a 1 M solution of NaOH (3×20 mL)
  4. dry with materialThe organic phase was dried over MgSO4
  5. customthe solvent removed by evaporation under reduced pressure
  6. customthe crude material used in the next step without further purification

出典と根拠

ORDレコード
ord-3a1d46ce7c49490da316f8b886fb5117
出典データセット
uspto-grants-2010_01
特許番号
US07645753B2

反応ノート

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