HCID 66660290, compound → HCID 58056584, compound

HRID 383795Notes

Reaction equation

HRID 383795 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:11][C@H:10]([C:20](O)=[O:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[CH:14]1([C@H:12]2[CH2:11][C@@H:10]([CH2:20][OH:21])[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13]2)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

3

Reactant 1

HCID 66660290HCID 66660290, compound

Product 1

HCID 58056584HCID 58056584, compoundYield 131.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the solution of cis-1-(tert-butoxycarbonyl)-5-cyclohexylpiperidine-3-carboxylic acid (400.9 mg) in THF (10 ml) was added 2 M solution of borane dimethylsulfide complex in THF (4.0 ml) at −15° C. under stirring. After stirring for 4 hours, The mixture was quenched by addition of MeOH. The resulting mixture was allowed to be room temperature and concentrated. To the residue was added saturated aqueous solution of NH4Cl and extracted with EtOAc. The extract was washed with brine, dried over MgSO4 and concentrated. The residue was purified with silica gel column chromatography (eluent: CHCl3/MeOH=99/1˜90/10) to give tert-butyl cis-3-cyclohexyl-5-(hydroxymethyl)piperidine-1-carboxylate (505.1 mg) as a colorless oil.

Workup

  1. stirringAfter stirring for 4 hours
  2. customThe mixture was quenched by addition of MeOH
  3. customto be room temperature
  4. concentrationconcentrated
  5. additionTo the residue was added saturated aqueous solution of NH4Cl
  6. extractionextracted with EtOAc
  7. washThe extract was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe residue was purified with silica gel column chromatography (eluent: CHCl3/MeOH=99/1˜90/10)

Sources & evidence

ORD record
ord-2d5c051641af4d029c6e1a09a39f9ff9
Source dataset
uspto-grants-2013_02
Patent number
US08367690B2

Reaction notes

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