Diethyl Ether → (S)-Methyl 4-(1-((tert-butoxycarbonyl)amino)ethyl)benzoate
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.CN(C)[CH:56]=[O:57].C[CH2:60][O:61]CC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO>[C:13]([O:12][C:11]([NH:10][C@H:8]([C:5]1[CH:6]=[CH:7][C:2]([C:60]([O:57][CH3:56])=[O:61])=[CH:3][CH:4]=1)[CH3:9])=[O:17])([CH3:16])([CH3:15])[CH3:14]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A mixture of tert-butyl [(1S)-1-(4-bromophenyl)ethyl]carbamate (step 3, 14.73 g, 49.1 mmol), 1,3-bis(diphenylphosphino)-propane (2.03 g, 4.91 mmol), palladium (II) acetate (1.10 g, 4.91 mmol), triethylamine (20.5 mL, 147 mmol), N,N-dimethylforamide (120 mL) and methanol (180 mL) was stirred at 80° C. for 16 h under carbon monoxide atmosphere. After cooling to room temperature, the mixture was diluted with ether (800 mL) and washed with water (500 mL×3). The organic layer was dried over magnesium sulfate and evaporated. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (5:1) to afford 12.83 g (94%) of the title compound as white solids:
Workup
- temperatureAfter cooling to room temperature
- washwashed with water (500 mL×3)
- dry with materialThe organic layer was dried over magnesium sulfate
- customevaporated
- customThe residue was purified
- customby flush column chromatography on silica gel eluting with hexane/ethyl acetate (5:1)
Sources & evidence
- ORD record
- ord-f8786a362efd4c12ace8026facb1a6f8
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07534914B2
Reaction notes
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