Hydrochloric Acid → HCID 59382893, compound

HRID 2355373Notes

Reaction equation

HRID 2355373 reaction equation
C([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C@@:14]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)([OH:22])[CH2:15][CH2:16][CH2:17][C:18]([F:21])([F:20])[CH3:19])[CH2:9]1)(OC(C)(C)C)=O.Cl>C(#N)C>[Cl:29][C:25]1[CH:24]=[C:23]([C@:14]([C@@H:10]2[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)([OH:22])[CH2:15][CH2:16][CH2:17][C:18]([F:21])([F:20])[CH3:19])[CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 671914461,1-Dimethylethyl (3R)-3-[(1S)-1-(3-chlorophenyl)-5,5-difluoro-1-hydroxyhexyl]-1-piperidinecarboxylate

Product 1

HCID 59382893HCID 59382893, compoundYield 52.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Boc-(S)-1-(3-chlorophenyl)-5,5-difluoro-1-((R)-piperidin-3-yl)hexan-1-ol (70 mg, 0.16 mmol) was dissolved in acetonitrile (16 mL) and 2M aq HCl (16 mL) and allowed to stir at rt overnight. The solvent was removed under high vacuum. The crude material was redissolved in CH2Cl2 and washed with satd NaHCO3 2×. The aqueous layer was extracted with CH2Cl2 3×. The combined organic layers were washed with brine and dried over sodium sulfate. After removing solvent under vacuum (S)-1-(3-chlorophenyl)-5,5-difluoro-1-((R)-piperidin-3-yl)hexan-1-ol was isolated as an oil (28 mg) MS m/z 332 (M+H+).

Workup

  1. customThe solvent was removed under high vacuum
  2. dissolutionThe crude material was redissolved in CH2Cl2
  3. washwashed with satd NaHCO3 2×
  4. extractionThe aqueous layer was extracted with CH2Cl2 3×
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customAfter removing solvent under vacuum (S)-1-(3-chlorophenyl)-5,5-difluoro-1-((R)-piperidin-3-yl)hexan-1-ol

Sources & evidence

ORD record
ord-2ad1751b57424d5589461a17236d3a61
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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