4-tert-Butoxycarbonylamino-4-(4-isopropyl-phenylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester → [4-(4-Isopropyl-phenylcarbamoyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 1949085Notes

Reaction equation

HRID 1949085 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][C:14]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])([C:17](=[O:28])[NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]([CH3:27])[CH3:26])=[CH:21][CH:20]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>CO.[Pd]>[C:33]([O:32][C:30](=[O:31])[NH:29][C:14]1([C:17](=[O:28])[NH:18][C:19]2[CH:24]=[CH:23][C:22]([CH:25]([CH3:26])[CH3:27])=[CH:21][CH:20]=2)[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1)([CH3:35])([CH3:34])[CH3:36]

Participants

4

Reactant 1

HCID 669213864-tert-Butoxycarbonylamino-4-(4-isopropyl-phenylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 66921345[4-(4-Isopropyl-phenylcarbamoyl)-piperidin-4-yl]-carbamic acid tert-butyl esterYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2.84 g (6 mmol) 4-tert-Butoxycarbonylamino-4-(4-isopropyl-phenylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester (example 82, step 1) in 80 mL methanol was hydrogenated with H2 over Pd/C (10%) for 2 h at room temperature. The mixture was filtered off and evaporated to dryness to yield 1.94 g (94%) of the title compound as off-white crystals. MS (m/e): 362.4 [(M+H)+].

Workup

  1. filtrationThe mixture was filtered off
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-10fc16e31ec442ca8f7dfed152680ba4
Source dataset
uspto-grants-2013_03
Patent number
US08399676B2

Reaction notes

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