HCID 11628336, compound → HCID 11698610, compound

HRID 1993977Notes

Reaction equation

HRID 1993977 reaction equation
C([N:8]1[CH2:12][C@H:11]2[C@H:13]([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[C@@H:14]([O:17][C@@H:18]([C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=3)[CH3:19])[O:15][CH2:16][C@@H:10]2[CH2:9]1)C1C=CC=CC=1.[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[F:33][C:30]([F:31])([F:32])[C:22]1[CH:21]=[C:20]([C@H:18]([O:17][C@H:14]2[O:15][CH2:16][C@@H:10]3[CH2:9][NH:8][CH2:12][C@H:11]3[C@@H:13]2[C:34]2[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=2)[CH3:19])[CH:25]=[C:24]([C:26]([F:29])([F:27])[F:28])[CH:23]=1

Participants

5

Reactant 2

HCID 11628336HCID 11628336, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 11698610HCID 11698610, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

(3aS,6R,7R,7aR)-2-Benzyl-6-{(1R)-1-[3,5-bis(trifluoromethyl)phenyl]ethoxy}-7-(4-fluorophenyl)octahydropyrano[3,4-c]pyrrole (example 1: 1.60 g, 2.82 mmol) was combined 0.75 g 20% Pd(OH)2 and suspended in 30 mL ethanol in a Parr apparatus. The reaction vessel was shaken vigorously under 45 psi hydrogen for 4 hr. The reaction mixture was filtered through a pad of celite and rinsed copiously with methanol. The volatiles were removed in vacuo and the crude residue was purified on silica gel and eluted with a combination of methanol/DCM (1-10% methanol/DCM linear gradient) which furnished the title compound. 1H-NMR (CD3OD): δ 1.38 (d, 3H, J=7.0 Hz), 1.90-2.10 (m, 2H), 2.47 (dd, 1H, J=10.5, 10.5 Hz), 2.56 (dd, 1H, J=10.5, 10.5 Hz), 2.65 (dd, 1H, J=8.0, 11.0 Hz), 2.75 (dd, 1H, J=6.5, 10.5 Hz), 3.11 (dd, 1H, J=6.5, 10.0 Hz), 3.56 (dd, 1H, J=10.5, 10.5 Hz), 4.24 (dd, 1H, J=4.0, 11.0 Hz), 4.37 (d, 1H, J=8.0 Hz), 5.07 (q, 1H, J=6.5 Hz), 6.96 (dd, 2H, J=9.0, 9.0 Hz), 7.16 (dd, 2H, J=5.5, 9.0 Hz), 7.20-7.30 (m, 5H), 7.38 (s, 2H), 7.75 (s, 1H) ppm. MS: (MH)+478.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washrinsed copiously with methanol
  3. customThe volatiles were removed in vacuo
  4. customthe crude residue was purified on silica gel
  5. washeluted with a combination of methanol/DCM (1-10% methanol/DCM linear gradient) which

Sources & evidence

ORD record
ord-43f8193c2c3d42cca9e05d7d58cf1317
Source dataset
uspto-grants-2010_01
Patent number
US07652058B2

Reaction notes

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