HCID 66650218, compound → HCID 66650028, compound

HRID 419689Notes

Reaction equation

HRID 419689 reaction equation
[C:1]([O:5][C:6](=[O:22])[C@@H:7]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-])=O)[CH:8]([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2]>CCO.[Ni]>[C:1]([O:5][C:6](=[O:22])[C@@H:7]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19])[CH:8]([CH3:10])[CH3:9])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 66650218HCID 66650218, compound

Product 1

HCID 66650028HCID 66650028, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of (2S)-3-methyl-2-(2-nitro-benzylamino)-butyric acid tert-butyl ester (1.753 g, 5.68 mmol) in EtOH (30 mL) was added Raney nickel (1.3 mL) and the reaction mixture was hydrogenated under balloon pressure for 2 hours. The catalyst was filtrated and the filtrate evaporated to give the sub-title compound as a yellow oil (1.573 g, 100%). 1H NMR (400 MHz CDCl3) δ 0.81-0.90 (6H, m), 1.55 (9H, s), 1.90 (1H, m), 2.89 (1H, d), 3.62 (1H, d), 3.86 (1H, d), 4.68 (2H, vbr s), 6.68 (2H, m), 7.02 (1H, d), 7.13 (1H, t).

Workup

  1. filtrationThe catalyst was filtrated
  2. customthe filtrate evaporated

Sources & evidence

ORD record
ord-b2ce6734509c49b1ae6c426e5218a672
Source dataset
uspto-grants-2012_01
Patent number
US08093392B2

Reaction notes

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