CID 71433830 → N-((1R,2S)-1-benzyl-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)pyrrolidin-2-one

HRID 587803Notes

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]([O:48][CH3:49])[CH:46]=2)[CH2:41][CH2:40][C:39]=1[N:50]1[CH2:54][CH2:53][CH2:52][C:51]1=[O:55])[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][CH:44]=[C:45]([O:48][CH3:49])[CH:46]=2)[CH2:41][CH2:40][C@@H:39]1[N:50]1[CH2:54][CH2:53][CH2:52][C:51]1=[O:55])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Chlorocyclooctadiene rhodium(I) dimer (3.70 mg, 15.0 μmol of Rh), Josiphos SL-J216-2 (10.16 mg, 16.0 μmol), and N-(1-benzyl-7-methoxy-3,4-dihydronaphthalen-2-yl)pyrrolidin-2-one (500.8 mg, 1.50 mmol) were combined in a glass-lined metal reactor, and the vessel was inerted with argon. Degassed methanol (5.0 ml) was added, and the mixture was agitated under 20 psi of argon at 50° C. for 20 min. The vessel was pressurized with 90 psig of hydrogen and stirred at 100° C. for 45 hrs. HPLC analysis indicated 99.8% conversion and 90.7% ee. The mixture was concentrated and diluted with water to yield 415 mg (yield: 82%) of the title compound.

Workup

stirringstirred at 100° C. for 45 hrs
concentrationThe mixture was concentrated
additiondiluted with water

Sources & evidence

ORD record: ord-2a504da920704bf8b22cc262159a750e
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09227901B2

Reaction notes

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