tert-butyl(1R)-1-benzyl-2-(benzylamino)ethylcarbamate → HCID 42645993, compound

HRID 403002Notes

Reaction equation

HRID 403002 reaction equation
[CH2:1]([C@@H:8]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:9][NH:10]CC1C=CC=CC=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[OH-].[OH-].[Pd+2]>[NH2:10][CH2:9][C@H:8]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 40539163tert-butyl(1R)-1-benzyl-2-(benzylamino)ethylcarbamate

Product 1

HCID 42645993HCID 42645993, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

The product from Example 70B (3.36 g, 9.9 mmol) in methanol (10 mL) was treated with 20% Pd(OH)2/C (wet) (335 mg) under a hydrogen atmosphere (4 atmospheres) at 50° C. After 3.25 hours, the solution was filtered and the filtrate was concentrated. The residue was dried under reduced pressure to provide the title compound as a white solid (2.46 g). 1H NMR (DMSO-d6) δ 7.32-7.12 (m, 5H), 6.54 (d, 1H), 3.53 (m, 1H), 2.79-2.69 (dd, 2H), 2.66-2.50 (m, 4H), 1.31 (s, 9H); MS (ESI+) m/z 251 (M+H)+.

Workup

  1. filtrationthe solution was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was dried under reduced pressure

Sources & evidence

ORD record
ord-25a891222b144035bf4d1803020b0c42
Source dataset
uspto-grants-2014_06
Patent number
US08741938B2

Reaction notes

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