1-Benzyl 4-methyl 4-((tert-butoxycarbonyl)amino)piperidine-1,4-dicarboxylate → Methyl 4-(((1,1-dimethylethoxy)carbonyl)amino)-4-piperidinecarboxylate

HRID 232012Notes

Reaction equation

HRID 232012 reaction equation
C([N:11]1[CH2:16][CH2:15][C:14]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12]1)(OCC1C=CC=CC=1)=O>CO.[OH-].[OH-].[Pd+2]>[C:25]([O:24][C:22]([NH:21][C:14]1([C:17]([O:19][CH3:20])=[O:18])[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

4

Reactant 1

HCID 145370781-Benzyl 4-methyl 4-((tert-butoxycarbonyl)amino)piperidine-1,4-dicarboxylate

Product 1

HCID 14537079Methyl 4-(((1,1-dimethylethoxy)carbonyl)amino)-4-piperidinecarboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.56 g (4.0 mmoles) of N-carbobenzyloxy-4-(tert-butyloxycarbonylamino)-4-carbomethoxy-piperidine in 150 ml of methanol was hydrogenated at 50 psi (20° C.) on a Parr apparatus for 18 hours, using 1.01 g of Pearlman's catalyst (palladium hydroxide on carbon; palladium hydroxide content 20%, water content 31%). The catalyst was filtered and the filtrate concentrated in vacuo to afford the title compound (1.02 g; 100% yield) as a colorless amorphous solid. 1Hnmr (60 mHz, CDCl3) delta 1.23 (9H, s), 1.8-2.35 (4H, broad m), 2.78-3.23 (4H, broad m), 3.77 (3H, s).

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-284c0505357c46ca9f543b4920104aa5
Source dataset
uspto-grants-1989_07
Patent number
US04851388

Reaction notes

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