HCID 54289398, compound → 1,1-Dimethylethyl 4-(methylamino)butanoate

HRID 1277296Notes

Reaction equation

HRID 1277296 reaction equation
C(OC([CH:11]([NH:21][CH3:22])[CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=O)C1C=CC=CC=1>CO.[C].[Pd]>[CH3:22][NH:21][CH2:11][CH2:12][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

4

Reactant 1

HCID 54289398HCID 54289398, compound

Product 1

HCID 147603141,1-Dimethylethyl 4-(methylamino)butanoateYield 98.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In methanol (70 ml) was dissolved tert-butyl 4-[(benzyloxy)carbonyl]-4-methylaminobutyrate (6.06 g), and to the mixture was added 10% palladium-carbon (580 mg). Under hydrogen atmosphere, the mixture was stirred at room temperature for 3 hours, and 10% palladium-carbon was removed. The solvent was evaporated under reduced pressure to give tert-butyl 4-methylaminobutyrate (3.35 g, 98%). 1H NMR (200 MHz, CDCl3) δ 1.45 (9H, s), 1.72 (1H, brs), 1.77 (2H, quint, J=7.2 Hz), 2.27 (2H, t, J=7.3 Hz), 2.43 (3H, s), 2.61 (2H, t, J=7.1 Hz).

Workup

  1. custom10% palladium-carbon was removed
  2. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-af2809b087e3434db1ecccfae04706f6
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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