Methanol → 4-{[4-(3,4-Dichlorophenoxy)piperidin-1-yl]methyl}cyclopentane-1,2-diol

HRID 1727844Notes

Reaction equation

HRID 1727844 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([CH:14]2[CH2:18][CH:17]([OH:19])[CH:16]([OH:20])[CH2:15]2)=O)[CH2:8][CH2:7]1.CO>B.O1CCCC1>[NH3:9].[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][C:23]=1[Cl:24])[O:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH:14]2[CH2:18][CH:17]([OH:19])[CH:16]([OH:20])[CH2:15]2)[CH2:8][CH2:7]1

Participants

6

Reactant 2

HCID 887MethanolHCID 68933653HCID 68933653, compound

Product 2

HCID 222AmmoniaHCID 666157064-{[4-(3,4-Dichlorophenoxy)piperidin-1-yl]methyl}cyclopentane-1,2-diolYield 213.6%

Reagents, catalysts & solvents 2

HCID 6331BoraneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The more polar isomer of 4-[[4-(3,4dichlorophenoxy)-1-piperidinyl]carbonyl]-1,2-cyclopentanediol (0.71 g) was dissolved in a solution of borane in tetrahydrofuran (16 mL of 1M solution) and the mixture was heated to reflux for 1.5 h. Methanol (10 mL) was added and the solution was heated under reflux for 1 h. The volatile components were evaporated and the residue was loaded onto an HPLC SCX cartridge in methanol and eluted with methanol, then with 0.7M ammonia in methanol to give the title compound (0.73 g) as an oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1.5 h
  3. temperaturethe solution was heated
  4. temperatureunder reflux for 1 h
  5. customThe volatile components were evaporated
  6. washeluted with methanol

Sources & evidence

ORD record
ord-49e8f28b9a4a49efa43dd607e81419d1
Source dataset
uspto-grants-2009_02
Patent number
US07495013B2

Reaction notes

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