HCID 66783258, compound → HCID 44602502, compound

HRID 1096282Notes

Reaction equation

HRID 1096282 reaction equation
C([Si](C)(C)[O:6][C@@H:7]1[CH2:14][N:13]([CH2:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[C:26]([Cl:34])[CH:25]=3)[C@@H:20]([CH3:35])[C:19]2=[O:36])[CH2:12][CH2:11][C:8]21[CH2:10][CH2:9]2)(C)(C)C>CC#N>[Cl:34][C:26]1[CH:25]=[C:24]([N:21]2[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][CH2:15][N:13]3[CH2:12][CH2:11][C:8]4([CH2:10][CH2:9]4)[C@H:7]([OH:6])[CH2:14]3)[C:19](=[O:36])[C@@H:20]2[CH3:35])[CH:29]=[CH:28][C:27]=1[C:30]([F:33])([F:31])[F:32]

Participants

3

Reactant 1

HCID 66783258HCID 66783258, compound

Product 1

HCID 44602502HCID 44602502, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (S)-1-{3-[(S)-4-(tert-butyl-dimethyl-silanyloxy)-6-aza-spiro[2.5]oct-6-yl]-propyl}-4-(3-chloro-4-trifluoromethyl-phenyl)-3-methyl-piperazin-2-one (65 mg, 0.11 mmol) and hydrogen fluoride pyridine complex (70% HF; 0.26 mL) in CH3CN (3 mL) was heated at 50° C. for 16 h, then partitioned between EtOAc and sat. aq. NaHCO3 solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (IST Isolute® Flash NH2; EtOAc-MeOH gradient) afforded the title compound (29 mg, 56%) in a diastereomeric ratio of 97:3. Colourless gum, MS: 460.3 (M+H)+.

Workup

  1. custompartitioned between EtOAc and sat. aq. NaHCO3 solution
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-0ec78c8268ac446ab0932b3c0a2c3af6
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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