Acetic Acid → HCID 68669887, compound

HRID 2070974Notes

Reaction equation

HRID 2070974 reaction equation
C=O.N[C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[BH3-][C:20]#[N:21].[Na+].[CH3:23]C(O)=O>CC#N>[CH3:23][N:21]([CH3:20])[C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 10775412tert-butyl N-((3-aminophenyl)methyl)carbamate

Product 1

HCID 68669887HCID 68669887, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

CH2O (aq. 37%, 1.57 mL, 21.1 mmol, 10 eq) was added to a stirred solution of tert-butyl 3-aminobenzylcarbamate (0.47 g, 2.1 mmol, 1 eq) in 10 mL CH3CN. The resulting solution was treated with NaBH3CN (0.42 g, 6.3 mmol, 3 eq) followed by the dropwise addition of HOAc to pH=7. The solution was stirred for 1 h adding HOAc occasionally to keep the pH close to 7. The reaction was concentrated in vacuo and the resulting residue was diluted with sat. NaHCO3 and extracted into EtOAc (×1). The organic layer was washed with water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent removed in vacuo. Purification via flash chromatography on silica gel yielded 0.39 g (1.6 mmol, 74% yield) of tert-butyl 3-(dimethylamino)benzylcarbamate.

Workup

  1. customclose to 7
  2. concentrationThe reaction was concentrated in vacuo
  3. additionthe resulting residue was diluted with sat. NaHCO3
  4. extractionextracted into EtOAc (×1)
  5. washThe organic layer was washed with water (×3), brine (×1)
  6. dry with materialdried over Na2SO4
  7. filtrationThe inorganics were filtered off
  8. customthe solvent removed in vacuo
  9. customPurification via flash chromatography on silica gel

Sources & evidence

ORD record
ord-4df860f8f6b84b12860050f6d1db15dd
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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