CID 71433830 → N-((1R,2S)-1-benzyl-7-bromo-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][CH:44]=[C:45]([Br:48])[CH:46]=2)[CH2:41][CH2:40][C:39]=1[NH:49][C:50](=[O:53])[CH2:51][CH3:52])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[H][H]>[Rh+].ClC1CCCCC=CC=1.C(O)C>[CH2:31]([C@@H:38]1[C:47]2[C:42](=[CH:43][CH:44]=[C:45]([Br:48])[CH:46]=2)[CH2:41][CH2:40][C@@H:39]1[NH:49][C:50](=[O:53])[CH2:51][CH3:52])[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 (0.217 g, 0.881 mmol of Rh), Josiphos SL-J216-2 (0.595 g, 0.926 mmol), and N-(1-benzyl-7-bromo-3,4-dihydronaphthalen-2-yl)propionamide (10.88 g, 29.4 mmol) were combined in a metal reactor, and the vessel was inerted with argon. Degassed ethanol (163 ml) was added, and the mixture was agitated under argon for 30 min at 50° C. The vessel was pressurized with 60 psig of hydrogen and agitated at 55° C. for 14.5 hrs. HPLC analysis indicated 89.4% conversion and 93.8% ee. The mixture was concentrated, and the resulting solid was crystallized from MeOH to yield 7.41 g (yield: 68%) of the title compound.
Workup
- stirringagitated at 55° C. for 14.5 hrs
- concentrationThe mixture was concentrated
- customthe resulting solid was crystallized from MeOH
Sources & evidence
- ORD record
- ord-48e0a33ec1524d12ba330d599da8f15b
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09227901B2
Reaction notes
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