Acetic Acid → ethyl N-(3-methoxybenzyl)benzylaminoethanoate

HRID 1687933Notes

Reaction equation

HRID 1687933 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1)[CH3:14]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 115693-MethoxybenzaldehydeHCID 80908N-Benzylglycine ethyl esterHCID 5003444Sodium cyanoborohydride

Product 1

HCID 13760251ethyl N-(3-methoxybenzyl)benzylaminoethanoateYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl N-benzyl-glycinate (34.1 g, 176 mmol) and m-anisaldehyde (11.0 g, 80.8 mmol) in methanol (500 mL) was added acetic acid (12.1 mL, 202 mmol) followed by sodium cyanoborohydride (3.4 g, 54 mmol). The mixture was stirred at ambient temperature for 2.5 hours whereupon LCMS analysis showed completion of the reaction. The solvent was removed on a rotary evaporator and the residue was dissolved in ethyl acetate, washed with saturated sodium bicarbonate to neutrality. The organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. Flash chromatography over silica gel (CH2Cl2) gave 21.5 g (85% of [benzyl-(3-methoxy-benzyl)-amino]-acetic acid ethyl ester as a colorless oil. 1H NMR (400 MHz, DMSO-d6) δ 7.35 (m, 4H), 7.25 (m, 2H), 6.93 (m, 2H), 6.82 (d, J=9 Hz, 1H), 4.10 (q, J=7 Hz, 2H), 3.74 (s, 3H), 3.70 (s, 2H), 3.32 (s, 2H), 3.24 (s, 2H), 1.18 (t, J=7 Hz, 3H; MS (m/e) 314 (M+1).

Workup

  1. customcompletion of the reaction
  2. customThe solvent was removed on a rotary evaporator
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with saturated sodium bicarbonate to neutrality
  5. washThe organic phase was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7381f6209bbe4cc9905242f185893560
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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