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

HRID 1990865Notes

Reaction equation

HRID 1990865 reaction equation
[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

Participants

3

Reactant 2

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

Product 1

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

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3a1d46ce7c49490da316f8b886fb5117
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

Loading…