Formaldehyde → Tert-butyl 2-(benzyl(methyl)amino)ethylcarbamate

HRID 1027648Notes

Reaction equation

HRID 1027648 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]=O>C([O-])(O)=O.[Na+]>[CH2:1]([N:8]([CH3:19])[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 10634443N-Benzyl-N'-boc-ethylenediamine

Product 1

HCID 50999034Tert-butyl 2-(benzyl(methyl)amino)ethylcarbamateYield 46.8%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of tert-butyl 2-(benzylamino)ethylcarbamate (2.8 g, 11.2 mmol) and 37% aqueous CH2O (1.0 mL, 11.2 mmol) in 1,2-dicholoroethane (35 mL) at RT was added NaHB(AcO)3 (3.7 g, 11.2 mmol). The mixture was stirred (RT, 16 h), diluted with saturated aqueous NaHCO3 (400 ml) and extracted with EA (3×300 ml). The organic layer was dried over MgSO4 and concentrated under reduced pressure to afford tert-butyl 2-(benzyl(methyl)amino)ethylcarbamate (1.38 g, 46.8%). 1HNMR (CDCl3): δ7.25 (m, 5H, CH), 3.5 (s, 2H, CH2), 3.3 (m, 2H, CH2), 2.48 (m, 2H, CH2), 2.2 (s, 3H, CH3), 1.4 (s, 9H, CH3).

Workup

  1. extractionextracted with EA (3×300 ml)
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-92d26551f617414ebf8e5813e96f3f08
Source dataset
uspto-grants-2014_05
Patent number
US08735379B2

Reaction notes

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