Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate → HCID 68701571, compound

HRID 2234166Notes

Reaction equation

HRID 2234166 reaction equation
O[CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[Cr](Cl)([O-])(=O)=[O:17].[NH+:21]1C=CC=[CH:23][CH:22]=1>ClCCl>[OH:17][CH2:23][CH2:22][NH:21][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 178418287HCID 178418287, compound

Product 1

HCID 68701571HCID 68701571, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(hydroxymethyl)piperidine-1-carboxylate (4.3 g) was dissolved in dichloromethane (50 ml) and pyridinium chlorochromate (6.46 g) was added. The reaction was stirred for 2 hours and filtered through a thin bed of silica eluting with ethyl acetate/hexane (⅓). The resulting aldehyde was dissolved in ethanol (20 mL) and ethanolamine (2.44 g) was added along with 10% palladium (Pd) on Carbon (100 mg). The reaction mixture was hydrogenated at 2.5 bar for 24 hours, filtered and concentrated. The residue was dissolved in methanol and passed through a SCX cartridge eluting with methanol. The product was eluted with 7N ammonia in methanol to afford the sub-titled compound (4.2 g) as an oil.

Workup

  1. filtrationfiltered through a thin bed of silica eluting with ethyl acetate/hexane (⅓)
  2. dissolutionThe resulting aldehyde was dissolved in ethanol (20 mL)
  3. additionethanolamine (2.44 g) was added along with 10% palladium (Pd) on Carbon (100 mg)
  4. waitThe reaction mixture was hydrogenated at 2.5 bar for 24 hours
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in methanol
  8. washeluting with methanol
  9. washThe product was eluted with 7N ammonia in methanol

Sources & evidence

ORD record
ord-215e1e3b94f14838bef7ad254d5bdb3b
Source dataset
uspto-grants-2010_05
Patent number
US07709511B2

Reaction notes

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