HCID 86723936, compound → HCID 86723935, compound

HRID 1475294Notes

Reaction equation

HRID 1475294 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14][CH3:15])[N:11]([CH2:16][C:17]([O:19]CC2C=CC=CC=2)=[O:18])[CH2:10][C@H:9]1[CH3:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14][CH3:15])[N:11]([CH2:16][C:17]([OH:19])=[O:18])[CH2:10][C@H:9]1[CH3:27])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86723936HCID 86723936, compound

Product 1

HCID 86723935HCID 86723935, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C (10%, 810 mg) was added to a solution of (2R,5S)-4-benzyloxycarbonylmethyl-5-ethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester (2.8 g, 7.6 mmol) in MeOH (50 mL). The suspension was stirred overnight under H2. and catalyst was removed via filtration through Celite and the filtrate was evaporated in vacuo to give the title compound (1.7 g) as a pale yellow solid. 1H NMR (DMSO-d6): 4.41-3.89 (1H, m), 3.89-3.64 (1H, m), 3.37-3.21 (1H, m), 3.21-3.05 (2H, m), 2.71-2.55 (2H, m), 2.54-2.42 (3H, m), 1.45-1.36 (9H, m), 1.16 (3H, d), 0.83 (3H, t). MS: [M+H]+=287.

Workup

  1. customand catalyst was removed via filtration through Celite
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-c9104f2108574f53a958b173f5025dcd
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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