(RS)-1,1-Dimethylethyl 4-(1,2-Dihydroxyethyl)-4-(phenylmethoxymethyl)-1-piperidinecarboxylate → Tert-butyl 4-(1,2-dihydroxyethyl)-4-(hydroxymethyl)piperidine-1-carboxylate

HRID 2213032Notes

Reaction equation

HRID 2213032 reaction equation
[OH:1][CH:2]([C:5]1([CH2:18][O:19]CC2C=CC=CC=2)[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)[CH2:3][OH:4]>[Pd].C(O)C>[OH:19][CH2:18][C:5]1([CH:2]([OH:1])[CH2:3][OH:4])[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 21955196(RS)-1,1-Dimethylethyl 4-(1,2-Dihydroxyethyl)-4-(phenylmethoxymethyl)-1-piperidinecarboxylate

Product 1

HCID 21955164Tert-butyl 4-(1,2-dihydroxyethyl)-4-(hydroxymethyl)piperidine-1-carboxylateYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A slurry of palladium on carbon (10%, 100 mg) in ethanol (10 mL) was added to a solution of (RS)-1,1-dimethylethyl 4-(1,2-dihydroxyethyl)-4-(phenylmethoxymethyl)-1-piperidinecarboxylate (Description 97, 1.05 g, 2.9 mmol) in ethanol (30 mL) and the mixture was shaken under hydrogen (50 psi) for 72 hours. The mixture was filtered through Celite™ and the solvent was evaporated under reduced pressure to give the title compound as a pale oil (615 mg, 77%). m/z (ES+) 276 (M+1).

Workup

  1. filtrationThe mixture was filtered through Celite™
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9edcad81c0d849c18086180391ca2512
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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