Methylamine → Benzyl [(2S)-3-aminobutan-2-yl]carbamate

HRID 2275810Notes

Reaction equation

HRID 2275810 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH:12]([CH3:26])[C@@H:13]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:14].CN>CO>[NH2:3][CH:12]([CH3:26])[C@@H:13]([NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:14]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86717898Benzyl [(2S)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butan-2-yl]carbamate

Product 1

HCID 83350014Benzyl [(2S)-3-aminobutan-2-yl]carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

600 mg of benzyl [(2S)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butan-2-yl]carbamate (Example 137A, 1.7 mmol, 1 equivalent) were suspended in 10 ml of methanol, and 2.9 ml of 40% strength aqueous methylamine solution (2.6 g, 34 mmol, 20 equivalent) were added at RT. The mixture was allowed to stand at RT overnight, and Extrelut® was then added and the mixture was concentrated. The residue was purified on a silica gel cartridge (Biotage Isolera SNAP Cartridge KP-Sil 25 g, mobile phase: dichloromethane/methanol from 95:5 to 0:100). This gave 293 mg (43% of theory) of the title compound.

Workup

  1. additionExtrelut® was then added
  2. concentrationthe mixture was concentrated
  3. customThe residue was purified on a silica gel cartridge (Biotage Isolera SNAP Cartridge KP-Sil 25 g, mobile phase: dichloromethane/methanol from 95:5 to 0:100)

Sources & evidence

ORD record
ord-c61a674462c341f69772bf5b44fc6a71
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

Loading…