Tert-butyl 4-(2-(benzyloxy)-3-(tert-butoxy)propyl]-4-hydroxy-1-piperidinecarboxylate → Tert-butyl 4-[2-(benzyloxy)-3-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylate

HRID 2300162

Reaction equation

HRID 2300162 reaction equation
[CH2:1]([O:8][CH:9]([CH2:25][O:26]C(C)(C)C)[CH2:10][C:11]1([OH:24])[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+]([O-])([O-])=O.[NH4+].[Ce]>C(#N)C>[CH2:1]([O:8][CH:9]([CH2:25][OH:26])[CH2:10][C:11]1([OH:24])[CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:21])[CH3:22])=[O:18])[CH2:15][CH2:16]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 22744588Tert-butyl 4-(2-(benzyloxy)-3-(tert-butoxy)propyl]-4-hydroxy-1-piperidinecarboxylateHCID 57418452Ammonium cerium-nitrate

Product 1

HCID 22744648Tert-butyl 4-[2-(benzyloxy)-3-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylateYield 26.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.36 g of tert-butyl 4-[2-(benzyloxy)-3-(tert-butoxy)propyl]-4-hydroxy-1-piperidinecarboxylate was dissolved in 40 ml acetonitrile, 426 mg of cerium ammonium nitrate was added thereto, and the mixture was stirred at room temperature overnight. Silica gel was added to the reaction solution, and then it was evaporated. It was purified by adsorptive silica gel charged in a non-adsorptive silica gel column with hexane-ethyl acetate to give 547 mg of tert-butyl 4-[2-(benzyloxy)-3-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylate.

Workup

  1. additionSilica gel was added to the reaction solution
  2. customit was evaporated
  3. customIt was purified by adsorptive silica gel
  4. additioncharged in a non-adsorptive silica gel column with hexane-ethyl acetate

Sources & evidence

ORD record
ord-8d22fd94ad45462797cbfecb71441228
Source dataset
uspto-grants-2002_12
Patent number
US06498159B1

Linked notes

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