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

HRID 587798Notes

Reaction equation

HRID 587798 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[NH:50][C:51](=[O:54])[CH2:52][CH3:53])[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[NH:50][C:51](=[O:54])[CH2:52][CH3:53])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 71433830CID 71433830HCID 86707884HCID 86707884, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 72946309N-((1R,2S)-1-benzyl-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propionamideYield 96.6%

Reagents, catalysts & solvents 2

HCID 178478078HCID 178478078, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Chlorocyclooctadiene rhodium(I) dimer (0.802 g, 1.63 mmol, 3.25 mmol of Rh), Josiphos SL-J216-2 (2.199 g, 3.42 mmol), and N-(1-benzyl-7-methoxy-3,4-dihydronaphthalen-2-yl)propionamide (440 g, 1.37 mol) were combined in a metal reactor, and the vessel was inerted with argon. Degassed methanol (4.40 I) was added, then the mixture was stirred under argon at 50° C. for 20 min. The vessel was pressurized with 60 psig of hydrogen and stirred at 55° C. for 40 hrs. HPLC analysis indicated complete conversion and 95.9% ee. The methanol solution of crude reduction product was concentrated and triturated with heptane to yield 428.2 g (yield: 91%) of the title compound.

Workup

  1. stirringstirred at 55° C. for 40 hrs
  2. concentrationThe methanol solution of crude reduction product was concentrated
  3. customtriturated with heptane

Sources & evidence

ORD record
ord-973574c18544471b8c3341adc5d5cad3
Source dataset
uspto-grants-2016_01
Patent number
US09227901B2

Reaction notes

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