Lithium Chloride → Phenyl 4-(1,3-dihydroxypropan-2-yl)-3-fluorophenylcarbamate
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])[CH:5]=[CH:4][C:3]=1[CH:18]([C:23](OC)=[O:24])[C:19](OC)=[O:20].[BH4-].[Na+].[Cl-].[Li+]>C(O)C.C1COCC1>[OH:24][CH2:23][CH:18]([C:3]1[CH:4]=[CH:5][C:6]([NH:8][C:9](=[O:10])[O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:2]=1[F:1])[CH2:19][OH:20]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of dimethyl 2-(2-fluoro-4-(phenoxycarbonylamino)phenyl)malonate (3.0 g, 8.31 mmol, 1.0 eq) in ethanol (15 mL) and THF (15 mL) was added NaBH4 (621 mg, 16.62 mmol, 2.0 eq) followed by lithium chloride (705 g, 16.62 mmol, 2.0 eq) at 0° C. and the mixture was stirred at 0° C. for 5 h. The solvent was evaporated and the residue diluted with water (30 mL) and extracted with EtOAc (2×50 mL). The organic layer was separated, washed with brine, dried over Na2SO4 and evaporated. The residue was purified by CC using MeOH/DCM (1:19) as eluent to get phenyl 4-(1,3-dihydroxypropan-2-yl)-3-fluorophenylcarbamate (482 mg, 19%, white solid; TLC system: MeOH/DCM (1:9), Rf: 0.6)
Workup
- customThe solvent was evaporated
- additionthe residue diluted with water (30 mL)
- extractionextracted with EtOAc (2×50 mL)
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried over Na2SO4
- customevaporated
- customThe residue was purified by CC
Sources & evidence
- ORD record
- ord-2c55536ac0464644b2641751dfe9d37f
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08946204B2
Reaction notes
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