Borane;tetrahydrofuran → Methyl 3-(hydroxymethyl)-5-[methyl(methylsulfonyl)amino]benzoate
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([N:14]([CH3:19])[S:15]([CH3:18])(=[O:17])=[O:16])[CH:13]=1)[C:8](O)=[O:9])=[O:4].B.C1COCC1.C(O)(=O)C.O>C1COCC1>[OH:9][CH2:8][C:7]1[CH:6]=[C:5]([CH:13]=[C:12]([N:14]([CH3:19])[S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=1)[C:3]([O:2][CH3:1])=[O:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
To a stirring solution of 234 mg of 3-(methoxycarbonyl)-5-(N-methylmethylsulfonamido)benzoic acid in 10 mL of THF at r.t. was added 1.2 mL of BH3.THF (1.0 M in THF). After the solution was stirred at 75° C. for 3 h, 3 mL of acetic acid:H2O (1:1) was added and stirring was continued until bubbling ceased. Saturated NaHCO3 solution was added to a pH=7, and the solution was concentrated. Water was added, and the aqueous layer was extracted with EtOAc (2×). The combined extracts were washed with water and brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (1.5% MeOH/CHCl3) provided 191 mg of methyl 3-(hydroxymethyl)-5-(N-methylmethylsulfonamido)benzoate as a pale yellow oil in 86% yield.
Workup
- stirringstirring
- customuntil bubbling
- additionSaturated NaHCO3 solution was added to a pH=7
- concentrationthe solution was concentrated
- additionWater was added
- extractionthe aqueous layer was extracted with EtOAc (2×)
- washThe combined extracts were washed with water and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customPurification by flash silica gel chromatography (1.5% MeOH/CHCl3)
Sources & evidence
- ORD record
- ord-874fb8c048114fd48054e3d11314351f
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08299267B2
Reaction notes
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