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

HRID 919134Notes

Reaction equation

HRID 919134 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-839a01ab59424a689201cdf73333fc7e
Source dataset
uspto-grants-2016_03
Patent number
US09272984B2

Reaction notes

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