tert-butyl 4-[1-(N'-benzyloxycarbonyl-hydrazinocarbonyl)-4-chlorobutan-1-yl]piperidine-1-carboxylate → Tert-butyl 4-[4-chloro-1-hydrazinocarbonyl-butan-1-yl]piperidine-1-carboxylate

HRID 546709Notes

Reaction equation

HRID 546709 reaction equation
C(OC([NH:11][NH:12][C:13]([CH:15]([CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)[CH2:16][CH2:17][CH2:18][Cl:19])=[O:14])=O)C1C=CC=CC=1>CO.[C].[Pd]>[Cl:19][CH2:18][CH2:17][CH2:16][CH:15]([CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)[C:13]([NH:12][NH2:11])=[O:14]

Participants

4

Reactant 1

HCID 66839389tert-butyl 4-[1-(N'-benzyloxycarbonyl-hydrazinocarbonyl)-4-chlorobutan-1-yl]piperidine-1-carboxylate

Product 1

HCID 66839238Tert-butyl 4-[4-chloro-1-hydrazinocarbonyl-butan-1-yl]piperidine-1-carboxylateYield 100.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

10% palladium-carbon (50% wet, 200 mg) was added to a solution of tert-butyl 4-[1-(N′-benzyloxycarbonyl-hydrazinocarbonyl)-4-chlorobutan-1-yl]piperidine-1-carboxylate (928 mg) in methanol (15 ml), and the reaction solution was hydrogenated at normal pressure at room temperature for 4.5 hours. The catalyst is removed by filtration and the filtrate is concentrated under reduced pressure to obtain 663 mg of the title compound. The property value of the compound is as follows.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-7042997d60f54e6b9e6befd6f63572e1
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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