Acetaldehyde → Benzyl-2-[(1-cyanoethyl)amino]acetate hydrochloride

HRID 990705Notes

Reaction equation

HRID 990705 reaction equation
[Si]([C:5]#[N:6])(C)(C)C.[CH2:7]([O:14][C:15](=[O:18])[CH2:16][NH2:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[ClH:19].C([O-])(O)=O.[Na+].[CH:25](=O)[CH3:26].CCO>C(Cl)Cl.CCOC(C)=O>[ClH:19].[CH2:7]([O:14][C:15](=[O:18])[CH2:16][NH:17][CH:25]([C:5]#[N:6])[CH3:26])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

9

Reactant 6

HCID 177AcetaldehydeHCID 313Hydrochloric Acid2×HCID 702EthanolHCID 82115Trimethylsilyl cyanideHCID 409140Benzyl glycinateHCID 516892Sodium Bicarbonate

Product 1

HCID 18470875Benzyl-2-[(1-cyanoethyl)amino]acetate hydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

TMSCN (4.27 ml, 32 mmol) was added cautiously (reaction is exothermic) to a stirred solution of glycine benzyl ester (5.3 g, 32 mmol, prepared from the HCl salt by partitioning between EtOAc and NaHCO3 solution) and acetaldehyde (1.8 ml, 32 mmol) in methylene chloride (11 ml). After 4 h the volatiles were removed in vacuo and the residue was taken up in EtOAc and was washed with brine, dried (Na2SO4) and evaporated in vacuo to an oil. The oil was redissolved in EtOAc and 9.9 M HCl in EtOH (38.4 mmol) was added to give a crystalline precipitate which was isolated by filtration and washing with EtOAc, to give 1-11: 1H NMR (CDCl3) δ1.49 (d, J=7.1 Hz, 3 H, CH3), 3.54 (d, J=17.3 Hz, 1 H, CHAHB), 3.64 (d, J=17.3 Hz, 1 H, CHAHB), 3.74 (q, J=7.0 Hz, 1 H, a-CH), 5.18 (s, 2 H, CH2O), 7.36 (s, 5 H, Ph).

Workup

  1. customAfter 4 h the volatiles were removed in vacuo
  2. washwas washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated in vacuo to an oil
  5. dissolutionThe oil was redissolved in EtOAc
  6. customto give a crystalline precipitate which
  7. customwas isolated by filtration
  8. washwashing with EtOAc
  9. customto give 1-11

Sources & evidence

ORD record
ord-68d065a03ecc4c7f894a3bacad28c2e0
Source dataset
uspto-grants-2002_10
Patent number
US06462050B1

Reaction notes

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