Ammonium formate → Methyl {3-[(2R)-2-aminopropyl]phenyl}acetate
Reaction equation
Cl.[CH3:2][O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][C@H:13]([NH:15][C@@H](C2C=CC=CC=2)C)[CH3:14])[CH:7]=1.C([O-])=O.[NH4+]>>[CH3:2][O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][C@H:13]([NH2:15])[CH3:14])[CH:7]=1Participants
Procedure
A solution of methyl[3-((2R)-2-{[(1R)-1-phenyl-ethyl]-amino}-propyl)-phenyl]-acetate hydrochloride (Preparation 26) (7.69 g, 22 mmol) and ammonium formate (6.94 g, 110 mmol) was heated to 75° C. in the presence of 20% palladium hydroxide-on-charcoal (Pd(OH)2/C, 2.00 g). After 90 minutes the reaction mixture was cooled to room temperature, filtered through arbocel and the filtrate concentrated in vacuo. The residue was partitioned between dichloromethane (100 ml) and 880 ammonia (100 ml) and the organic phase separated. The aqueous phase was extracted dichloromethane (100 ml) and the combined organic extracts dried (magnesium sulfate) and reduced in vacuo to give the title compound as a colourless oil (4.78 g). 1H NMR (400 MHz, CD3OD): δ 7.27-7.23 (1H, t), 7.13-7.09 (3H, m), 3.67 (3H, s), 3.63 (2H, s), 3.12-3.05 (1H, m), 2.67-2.57 (2H, m), 1.06 (3H, d) ppm. LRMS (electrospray): m/z [M+H]+ 208, [M+Na]+ 230.
Workup
- filtrationfiltered through arbocel
- concentrationthe filtrate concentrated in vacuo
- customThe residue was partitioned between dichloromethane (100 ml) and 880 ammonia (100 ml)
- customthe organic phase separated
- extractionThe aqueous phase was extracted dichloromethane (100 ml)
- dry with materialthe combined organic extracts dried (magnesium sulfate)
Sources & evidence
- ORD record
- ord-dba3f4bd913f41d3b440e73d571efac2
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07629358B2
Reaction notes
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