Ethyl ketone → HCID 22346143, compound

HRID 897112Notes

Reaction equation

HRID 897112 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:16][CH2:17][C:18](=O)[CH2:19][CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:17]([CH:18]([NH:2][CH2:3][CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH2:19][CH3:20])[CH3:16]

Participants

5

Reactant 3

HCID 7288Ethyl ketoneHCID 5049666Sodium triacetoxyborohydrideHCID 12715871Benzyl N-(2-aminoethyl)carbamate hydrochloride

Product 1

HCID 22346143HCID 22346143, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzyl 2-aminoethylcarbamate hydrochloride (2 g, 8.65 mmol) was dissolved in dichloromethane (50 ml) and 3-pentanone (3.7 ml, 35 mmol) was added. The reaction mixture was stirred for 1 hour at room temperature. Sodium triacetoxy borohydride (5.5 g, 26 mmol) was added and the reaction mixture was then stirred for 16 hours at room temperature. The solution was washed with saturated aqueous sodium hydrogen carbonate solution (40 ml). The dichloromethane phase was dried over anhydrous magnesium sulphate and the solvent was removed. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 concentrated aqueous ammonia (95:5:0.5 by volume). This gave the title compound as an oil (1.8 g).

Workup

  1. stirringthe reaction mixture was then stirred for 16 hours at room temperature
  2. washThe solution was washed with saturated aqueous sodium hydrogen carbonate solution (40 ml)
  3. dry with materialThe dichloromethane phase was dried over anhydrous magnesium sulphate
  4. customthe solvent was removed
  5. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-ad4bca17b7f34dfab7bbaf96d33d7646
Source dataset
uspto-grants-2005_07
Patent number
US06921753B2

Reaction notes

Loading…