Acetic Acid → Tert-butyl 3-(benzyl(methyl)amino)benzylcarbamate

HRID 2071006Notes

Reaction equation

HRID 2071006 reaction equation
C=O.[CH2:3]([NH:10][C:11]1[CH:12]=[C:13]([CH:23]=[CH:24][CH:25]=1)[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[BH3-][C:27]#N.[Na+].CC(O)=O>CC#N>[CH2:3]([N:10]([CH3:27])[C:11]1[CH:12]=[C:13]([CH:23]=[CH:24][CH:25]=1)[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:20])([CH3:21])[CH3:19])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68670447Tert-butyl 3-(benzylamino)benzylcarbamate

Product 1

HCID 68670737Tert-butyl 3-(benzyl(methyl)amino)benzylcarbamateYield 100.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

CH2O (aq, 37%) (0.112 ml, 0.12 g, 1.51 mmol, 2 eq) was added to a stirred solution of tert-butyl 3-(benzylamino)benzylcarbamate (0.2353 g, 0.753 mmol, 1 eq) in 5 ml CH3CN. After 10 min NaBH3CN (0.0615 g, 0.98 mmol, 1.3 eq) was added. The reaction was adjusted to pH {tilde over ( )} 7 with HOAc. After 2 h the solvent was removed in vacuo. The residue was diluted with saturated aqueous NaHCO3/EtOAc, and the layers were separated. The organic layer was washed with water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo to yield 0.2482 g (0.76 mmol, 100% yield) of tert-butyl 3-(benzyl(methyl)amino)benzylcarbamate.

Workup

  1. customAfter 2 h the solvent was removed in vacuo
  2. additionThe residue was diluted with saturated aqueous NaHCO3/EtOAc
  3. customthe layers were separated
  4. washThe organic layer was washed with water (×3), brine (×1)
  5. dry with materialdried over Na2SO4
  6. filtrationThe inorganics were filtered off
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-fee6e54db2f24d4f949b6aae21b248d3
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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