Tert-butyl 4-(4-(1-(benzyloxycarbonyl)azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate → Tert-butyl 4-(4-(azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate

HRID 873559Notes

Reaction equation

HRID 873559 reaction equation
C(OC([N:11]1[CH2:14][CH:13]([C:15]([NH:17][C:18]2[CH:37]=[CH:36][C:21]([O:22][CH:23]3[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]3)=[CH:20][CH:19]=2)=[O:16])[CH2:12]1)=O)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].O1CCCC1>[NH:11]1[CH2:14][CH:13]([C:15]([NH:17][C:18]2[CH:19]=[CH:20][C:21]([O:22][CH:23]3[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:27][CH2:28]3)=[CH:36][CH:37]=2)=[O:16])[CH2:12]1

Participants

4

Reactant 1

HCID 86702035Tert-butyl 4-(4-(1-(benzyloxycarbonyl)azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate

Product 1

HCID 86702036Tert-butyl 4-(4-(azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-(4-(1-(benzyloxycarbonyl)azetidine-3-carboxamido)phenoxy)piperidine-1-carboxylate (50 mg, 0.098 mmol) and tetrahydrofuran (5 ml) were added to 20% wet palladium hydroxide on carbon (10 mg, 0.071 mmol) in a 50 ml pressure bottle and the mixture was stirred for 16 hours at 30 psi and room temperature. The mixture was filtered through a nylon membrane and the filtrate was concentrated to give the title compound.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-2afe1bd1c8c94c4bbf7a5f785740ec48
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

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