HCID 57542646, compound → HCID 57542875, compound

HRID 2080290Notes

Reaction equation

HRID 2080290 reaction equation
[N:1]([CH2:4][C@H:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C@H:5]1[CH2:9][CH2:8][C:7](=[O:10])[N:6]1[CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:18])[CH3:20]

Participants

4

Reactant 1

HCID 57542646HCID 57542646, compound

Product 1

HCID 57542875HCID 57542875, compoundYield 65.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To (R)-tert-butyl 3-(2-(azidomethyl)-5-oxopyrrolidin-1-yl)propylcarbamate (300 mg, 1.01 mmol) in MeOH was added Pd/C. The mixture was the placed into an autoclave, degasses three times, charged with 30 psi of H2 and stirred at rt for 30 min. The mixture was the filtered and the filtrate was concentrated under reduced pressure to give (R)-tert-butyl 3-(2-(aminomethyl)-5-oxopyrrolidin-1-yl)propylcarbamate (180 mg of crude). LRMS (M+H+) m/z 198.1.

Workup

  1. additioncharged with 30 psi of H2
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8fcca4533c7b46c4b118a28a3fc48d37
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

Loading…