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

HRID 1990865노트

반응식

HRID 1990865 반응식
[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

참가 물질

3

반응물 2

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3a1d46ce7c49490da316f8b886fb5117
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645753B2

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