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

HRID 2305746Notes

Reaction equation

HRID 2305746 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 CHCl3 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 materialThe combined CHCl3 extracts were dried (K2CO3)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-7147dd12dc334889b3b77d9fae9d76e3
Source dataset
uspto-grants-2002_08
Patent number
US06441006B2

Reaction notes

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