HCID 86671111, compound → HCID 86671110, compound

HRID 1023647Notes

Reaction equation

HRID 1023647 reaction equation
C([O:8][C@H:9]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:24][CH2:23][C@:22]3([CH2:29][CH2:28][C@H:27]([OH:30])[C@@H:26]([O:31][CH2:32][C:33]([F:36])([F:35])[F:34])[CH2:25]3)[C:21]2=[O:37])=[CH:16][CH:15]=1)[C:10]([F:13])([F:12])[F:11])C1C=CC=CC=1>CO.[Pd]>[OH:30][C@H:27]1[CH2:28][CH2:29][C@@:22]2([C:21](=[O:37])[N:20]([C:17]3[CH:16]=[CH:15][C:14]([C@@H:9]([OH:8])[C:10]([F:11])([F:12])[F:13])=[CH:19][CH:18]=3)[CH2:24][CH2:23]2)[CH2:25][C@@H:26]1[O:31][CH2:32][C:33]([F:36])([F:34])[F:35]

Participants

4

Reactant 1

HCID 86671111HCID 86671111, compound

Product 1

HCID 86671110HCID 86671110, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(5R,7R,8R) and (5S,7S,8S)-2-(4-((R)-1-(benzyloxy)-2,2,2-trifluoroethyl)phenyl)-8-hydroxy-7-(2,2,2-trifluoroethoxy)-2-azaspiro[4.5]decan-1-one (174 mg, from Example 17) was dissolved in methanol (12 mL). Palladium on activated charcoal (10% Pd, 52 mg) was added and the mixture was purged with hydrogen (4 times). The reaction mixture was stirred under hydrogen at RT for 3 hours. The catalyst was removed by filtration over a filter aid (dicalite, Acros Organics), washed with additional ethyl acetate and the filtrate was evaporated. The crude material was purified by flash chromatography (gradient of ethyl acetate in heptane) to provide the title compound as a colorless foam (144 mg). MS (ESI): 442.3 (MH+).

Workup

  1. customthe mixture was purged with hydrogen (4 times)
  2. customThe catalyst was removed by filtration over a filter aid (dicalite, Acros Organics)
  3. washwashed with additional ethyl acetate
  4. customthe filtrate was evaporated
  5. customThe crude material was purified by flash chromatography (gradient of ethyl acetate in heptane)

Sources & evidence

ORD record
ord-b97f774cb2884b4288604db2d25d1ee4
Source dataset
uspto-grants-2014_05
Patent number
US08722721B2

Reaction notes

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