Ammonium Chloride → N-(2-Hydroxymethyl-indan-2-yl)-3-methyl-2-(2-methyl-propenyl)-benzamide
Reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:28])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[CH:24]=[C:25]([CH3:27])[CH3:26])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=O)C.[Li+].[BH4-].C1COCC1.[NH4+].[Cl-]>C1COCC1>[OH:3][CH2:4][C:6]1([NH:15][C:16](=[O:28])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[CH:24]=[C:25]([CH3:26])[CH3:27])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester (80 mg, 0.21 mmol) in anhydrous THF (1 mL) is added dropwise 2M LiBH4/THF (0.84 mL, 1.68 mmol) at RT under argon. The resulting solution is heated for 20 min at 100° C. on microwave. After cooling to room temperature, the reaction solution is poured into ice-water and aq. NH4Cl saturated solution to reach pH 7. The solution is extracted with EtOAc (50 mL×3). The combined EtOAc phase is washed with brine (10 ml×2), dried over Na2SO4 and concentrated. The residue is purified by HPLC to give a pure product (230) as white solid (58 mg, 82%).
Workup
- temperatureAfter cooling to room temperature
- extractionThe solution is extracted with EtOAc (50 mL×3)
- washThe combined EtOAc phase is washed with brine (10 ml×2)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe residue is purified by HPLC
Sources & evidence
- ORD record
- ord-bd2ede64a58a4b338e50b6cafcd2a704
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569535B2
Reaction notes
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