(R)-methyl 6-(4-fluoro-3-methylbenzyloxy)-2-azidohexanoate → (R)-methyl 6-(4-fluoro-3-methylbenzyloxy)-2-aminohexanoate
Reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]([N:17]=[N+]=[N-])[C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:3]=1[CH3:22]>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][C@@H:12]([NH2:17])[C:13]([O:15][CH3:16])=[O:14])=[CH:4][C:3]=1[CH3:22]Participants
4
Procedure
To a solution of (R)-methyl 6-(4-fluoro-3-methylbenzyloxy)-2-azidohexanoate (0.141 g, 0.453 mmol) in 10 mL of ethyl acetate, Pd on BaSO4 (0.070 g) was added. The mixture was flushed with H2 for 15 min and stirred at room temperature under H2 for 1 h. The reaction mixture was then filtered through a pad of Celite and washed with ethyl acetate. The filtrate was concentrated under reduced pressure. The residue was used in the next step without further purification (0.128 g, >99% yield). GC-MS: tR=4.0 min; m/z 283 (M+).
Workup
- customThe mixture was flushed with H2 for 15 min
- filtrationThe reaction mixture was then filtered through a pad of Celite
- washwashed with ethyl acetate
- concentrationThe filtrate was concentrated under reduced pressure
- customThe residue was used in the next step without further purification (0.128 g, >99% yield)
Sources & evidence
- ORD record
- ord-f6d814c72ece45169f70179df0eb62ae
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242174B2
Reaction notes
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