1-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylate → Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 380539Notes

Reaction equation

HRID 380539 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](OCC)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 27588121-Tert-butyl 4-ethyl piperidine-1,4-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateYield 36%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 39.2 gm (152 mMol) ethyl 1-tert-butoxycarbonylpiperidine-4-carboxylate in 600 mL diethyl ether were cautiously added 6.1 gm (152 mMol) lithium aluminum hydride in portions. The reaction mixture was stirred for about 1.5 hours after the addition was complete and was then carefully quenched with water. The reaction mixture was partitioned between diethyl ether and 5 N sodium hydroxide. The organic phase was washed with saturated aqueous sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure to provide about 24 gm of a waxy solid. This solid was crystallized from a mixture of diethyl ether and hexane to provide 11.7 gm (36%) of 1-tert-butoxycarbonyl-4-hydroxymethylpiperidine as a white solid.

Workup

  1. additionafter the addition
  2. customwas then carefully quenched with water
  3. customThe reaction mixture was partitioned between diethyl ether and 5 N sodium hydroxide
  4. washThe organic phase was washed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto provide about 24 gm of a waxy solid
  8. customThis solid was crystallized from a mixture of diethyl ether and hexane

Sources & evidence

ORD record
ord-6843faab5f3a462d80139b1de3132390
Source dataset
uspto-grants-2001_10
Patent number
US06303627B1

Reaction notes

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