Methylamine → Tert-butyl 3-(methylamino)propanoate

HRID 916550Notes

Reaction equation

HRID 916550 reaction equation
[CH3:1][NH2:2].[C:3]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(=[O:6])[CH:4]=[CH2:5].CCOC(C)=O.CO>CCO>[C:8]([O:7][C:3](=[O:6])[CH2:4][CH2:5][NH:2][CH3:1])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 15458tert-Butyl acrylateHCID 21584119Ethylacetate methanol

Product 1

HCID 14760311Tert-butyl 3-(methylamino)propanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A 33% solution of methylamine in EtOH (62 ml) is cooled to 0°. A solution of tert-butyl acrylate (12.8 g) in EtOH (50 ml) is added dropwise over 2.5 hours. This mixture is allowed to reach room temperature over night. All volatiles are removed under reduced pressure and the residue chromatographed on silicagel using first EtOAc and then EtOAc/MeOH 1:1 as eluent. 7.81 g of a slightly yellow oil are obtained. TLC (silicagel, EtOAc/MeOH 1:1): rf 0.13.

Workup

  1. waitto reach room temperature over night
  2. customAll volatiles are removed under reduced pressure
  3. customthe residue chromatographed on silicagel
  4. custom7.81 g of a slightly yellow oil are obtained

Sources & evidence

ORD record
ord-44874e311c14447fb4db49be5733d7ec
Source dataset
uspto-grants-2007_09
Patent number
US07271168B2

Reaction notes

Loading…