HCID 68714078, compound → HCID 55299712, compound

HRID 712483Notes

Reaction equation

HRID 712483 reaction equation
C([N:8]1[CH2:13][CH:12]2[CH:10]([CH:11]2[N:14]([CH3:16])[CH3:15])[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[CH3:15][N:14]([CH3:16])[CH:11]1[CH:12]2[CH:10]1[CH2:9][NH:8][CH2:13]2

Participants

4

Reactant 1

HCID 68714078HCID 68714078, compound

Product 1

HCID 55299712HCID 55299712, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-benzyl-N,N-dimethyl-3-azabicyclo[3.1.0]hexan-6-amine (1.80 g) in MeOH was added a catalytic amount of 20% Pd(OH)2/C. The reaction mixture was stirred for 3 h at room temperature under H2 and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 20:1 (v/v) DCM/MeOH) to afford the title compound as brown oil (0.74 g, 70.00%), HPLC: 99.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 127.5 (M+1); 1H NMR (400 MHz, CDCl3) δ: 1.25-1.28 (m, 3H), 1.72-1.76 (m, 2H), 2.31 (s, 6H), 3.19-3.29 (m, 2H) ppm.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was chromatographed with a silica gel column (eluting agent: 20:1 (v/v) DCM/MeOH)

Sources & evidence

ORD record
ord-e59d9c2cc5f84943b97313673ecb4d6d
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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