4-((4-((((3-Isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl)amino)methyl)piperidin-1-yl)methyl)tetrahydro-2H-pyran-4-carboxylic acid → Tert-butyl 4-(aminomethyl)oxane-4-carboxylate

HRID 736401

Reaction equation

HRID 736401 reaction equation
C(N1C2C=CC=CC=2N(C(NCC2CC[N:20]([CH2:23][C:24]3([C:30]([OH:32])=[O:31])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)CC2)=O)C1=O)(C)C>CO.[Ni]>[NH2:20][CH2:23][C:24]1([C:30]([O:32][C:24]([CH3:29])([CH3:25])[CH3:23])=[O:31])[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1

Participants

4

Reactant 1

HCID 117122634-((4-((((3-Isopropyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)carbonyl)amino)methyl)piperidin-1-yl)methyl)tetrahydro-2H-pyran-4-carboxylic acid

Product 1

HCID 67232834Tert-butyl 4-(aminomethyl)oxane-4-carboxylateYield 165.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 4-cyanotetrahydro-2H-pyran-4-carboxylate (18.95 g, 0.0897 mol, step 1) and Raney Ni (1.00 g) in methanol (200 mL) was hydrogenated (3 atm) at room temperature for 12 h. Then, the mixture was filtered through a pad of Celite, and the filtrate was concentrated in vacuo to give 16.01 g (83%) of the title compound as a yellow syrup.

Workup

  1. customat room temperature
  2. customfor 12 h
  3. filtrationThen, the mixture was filtered through a pad of Celite
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2eb95bd1651e48eabbf46abd2249888b
Source dataset
uspto-grants-2009_09
Patent number
US07595329B2

Linked notes

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