1-Tert-butyl 4-ethyl 4-(3-(benzyloxy)propyl)piperidine-1,4-dicarboxylate → 1-Tert-butyl 4-ethyl 4-(3-hydroxypropyl)piperidine-1,4-dicarboxylate

HRID 385534Notes

Reaction equation

HRID 385534 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][C:12]1([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)C1C=CC=CC=1>C(O)C.[C].[Pd]>[OH:8][CH2:9][CH2:10][CH2:11][C:12]1([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 578154051-Tert-butyl 4-ethyl 4-(3-(benzyloxy)propyl)piperidine-1,4-dicarboxylate

Product 1

HCID 578152391-Tert-butyl 4-ethyl 4-(3-hydroxypropyl)piperidine-1,4-dicarboxylateYield 109.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of 2.0 g of 1-tert-butyl 4-ethyl 4-(3-(benzyloxy)propyl)piperidine-1,4-dicarboxylate in 20 mL of ethanol, a suspension of 0.30 g of 10% palladium carbon in 2 mL of ethanol was added, and the mixture was stirred for 4 hours under a hydrogen atmosphere. The insoluble substance was filtered off, and the solvent was distilled off under reduced pressure to obtain 1.7 g of 1-tert-butyl 4-ethyl 4-(3-hydroxypropyl)piperidine-1,4-dicarboxylate as a colorless oily substance.

Workup

  1. additionwas added
  2. filtrationThe insoluble substance was filtered off
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-feb584a27ff449b69a7f8d2cce91226e
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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