tert-Butyl 4-oxopiperidine-1-carboxylate → Tert-butyl 4-hydroxypiperidine-1-carboxylate

HRID 1168990Notes

Reaction equation

HRID 1168990 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateYield 76.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(tert-butoxycarbonyl)-piperidin-4-one (4.90 g, 24.59 mmol), sodium borohydride (1.52 g, 40.18 mmol) and methanol was stirred for 10 h. The solvent was removed by rotary evaporation. The residue was treated with portions of acetone (4×20 mL) and evaporated each time on a rotary evaporator. Water (10 mL) was added and the product was extracted with CHCl3 (4×20 mL). The combined CHC13 extracts were dried (K2CO3), filtered and concentrated to afford 3.80 g (76.8%) of a thick syrup, that solidified upon standing.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. additionThe residue was treated with portions of acetone (4×20 mL)
  3. customevaporated each time
  4. customon a rotary evaporator
  5. additionWater (10 mL) was added
  6. extractionthe product was extracted with CHCl3 (4×20 mL)
  7. dry with materialwere dried (K2CO3)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-61bd14adabc04e43a43737d6d62266cd
Source dataset
uspto-grants-2003_09
Patent number
US06627648B1

Reaction notes

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