Methanol → HCID 66615698, compound

HRID 1878795Notes

Reaction equation

HRID 1878795 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([CH:15]3[CH2:19][CH:18]([OH:20])[CH:17]([OH:21])[CH2:16]3)=O)[CH2:9][CH2:8]2)=[C:4]([CH3:24])[CH:3]=1.B.CO>O1CCCC1>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH:15]3[CH2:16][CH:17]([OH:21])[CH:18]([OH:20])[CH2:19]3)[CH2:11][CH2:12]2)=[C:4]([CH3:24])[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 66615651HCID 66615651, compound

Product 1

HCID 66615698HCID 66615698, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-{[4-(4-Chloro-2-methylphenoxy)piperidin-1-yl]carbonyl}cyclopentane-1,2-diol (32.0 g) was dissolved in tetrahydrofuran (100 mL) and stirred, at room temperature, under nitrogen. Borane (1 M solution in THF; 300 mL) was added dropwise and then the reaction mixture was heated under reflux for 2 h. The reaction mixture was allowed to cool slightly and methanol (60 mL) was added carefully. Heating was resumed and continued overnight. The reaction mixture was concentrated in vacuo and the residue was purified using SCX resin:Non-basic impurities were eluted with methanol then product was eluted with 0.7 M ammonia in methanol. Solvent was removed in vacuo to give the title compound (30 g) as a mixture of 2 stereoisomers.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureto cool slightly
  4. temperatureHeating
  5. concentrationThe reaction mixture was concentrated in vacuo
  6. customthe residue was purified
  7. washNon-basic impurities were eluted with methanol
  8. washproduct was eluted with 0.7 M ammonia in methanol
  9. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-6b29d48bee764ef9a928b187b4751b13
Source dataset
uspto-grants-2012_11
Patent number
US08314127B2

Reaction notes

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