HCID 86602058, compound → HCID 86602059, compound

HRID 1295374Notes

Reaction equation

HRID 1295374 reaction equation
[F:1][C:2]([F:39])([F:38])[C:3]1[CH:4]=[C:5]([C@@H:13]([N:15]([CH3:37])[C:16]([C@@:18]23[CH2:23][CH:22]2[CH2:21][N:20](CC2C=CC=CC=2)[C@H:19]3[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:17])[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>[Pd].CC(O)=O>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([C@@H:13]([N:15]([CH3:37])[C:16]([C@@:18]23[CH2:23][CH:22]2[CH2:21][NH:20][C@H:19]3[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:17])[CH3:14])[CH:4]=[C:3]([C:2]([F:38])([F:39])[F:1])[CH:8]=1

Participants

4

Reactant 1

HCID 86602058HCID 86602058, compound

Product 1

HCID 86602059HCID 86602059, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To Intermediate 41, the more polar isomer (1S,2S)-3-benzyl-2-phenyl-3-aza-bicyclo[3.1.0]hexane-1-carboxylic acid [(S)-1-(3,5-bis-trifluoromethyl-phenyl)-ethyl]-methyl-amide (0.06 g, 0.11 mmol) was combined with palladium on carbon 20% (Pearlman's catalyst, 0.08 g) and HOAc (8 mL) and hydrogenated at 40 psi for 16 hours. The material was filtered thru celite and concentrated, then partitioned between saturated sodium bicarbonate solution and methylene chloride, the organics were washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude material was purified via prep tic using ETOAc as the eluant to give the title compound (0.027 g, 54% yield).

Workup

  1. filtrationThe material was filtered thru celite
  2. concentrationconcentrated
  3. custompartitioned between saturated sodium bicarbonate solution and methylene chloride
  4. washthe organics were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude material was purified via prep tic

Sources & evidence

ORD record
ord-5485a07ceac94ebbb095eeca17cbb06f
Source dataset
uspto-grants-2007_07
Patent number
US07241798B2

Reaction notes

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