CID 71433830 → N-((1R,2S)-1-benzyl-6-fluoro-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propionamide
Reaction equation
C[C@@H](PC)[C]1[C](P(C2C3C(=CC=CC=3)C=CC=2)C2C3C(=CC=CC=3)C=CC=2)[CH][CH][CH]1.[CH2:31]([C:38]1[C:47]2[C:42](=[CH:43][C:44]([F:50])=[C:45]([O:48][CH3:49])[CH:46]=2)[CH2:41][CH2:40][C:39]=1[NH:51][C:52](=[O:55])[CH2:53][CH3:54])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[H][H]>[Rh+].ClC1CCCCC=CC=1.CO>[CH2:31]([C@@H:38]1[C:47]2[C:42](=[CH:43][C:44]([F:50])=[C:45]([O:48][CH3:49])[CH:46]=2)[CH2:41][CH2:40][C@@H:39]1[NH:51][C:52](=[O:55])[CH2:53][CH3:54])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
Chlorocyclooctadiene rhodium(I) dimer (0.648 g, 2.63 mmol of Rh), Josiphos SL-J216-2 (1.779 g, 2.77 mmol), and N-(1-benzyl-6-fluoro-7-methoxy-3,4-dihydronaphthalen-2-yl)propionamide (93.96 g, 277 mmol) were combined in a metal reactor, and the vessel was inerted with argon. Degassed methanol (940 ml) was added, and the mixture was agitated under 20 psi of argon at 50° C. for 20 min. The vessel was pressurized with 60 psig of hydrogen and agitated at 55° C. for 14 hrs. HPLC analysis indicated complete conversion and 94.7% ee. The mixture was concentrated, and the resulting solid was precipitated from MeOH to yield 86.9 g (yield: 92%) of the title compound.
Workup
- stirringagitated at 55° C. for 14 hrs
- concentrationThe mixture was concentrated
- customthe resulting solid was precipitated from MeOH
Sources & evidence
- ORD record
- ord-45dd19af885e45e5b1a98d874a43cb1f
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227901B2
Reaction notes
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