Acetic Acid → HCID 68670712, compound

HRID 2071012Notes

Reaction equation

HRID 2071012 reaction equation
C=O.N[C:4]1[CH:5]=[C:6]([CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1)[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[BH3-][C:22]#[N:23].[Na+].[CH3:25]C(O)=O>CC#N.CCOCC.O>[CH3:25][N:23]([CH3:22])[C:4]1[CH:5]=[C:6]([CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1)[CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68670003HCID 68670003, compound

Product 1

HCID 68670712HCID 68670712, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21584184Diethylether waterSolvent

Procedure

CH2O (aq, 37%) (0.12 ml, 0.127 g, 1.56 mmol, 4 eq) was added to a stirred solution of tert-butyl 3-amino-5-methoxybenzylcarbamate (0.0975 g, 0.39 mmol, 1 eq) in 5 ml CH3CN. After 10 min NaBH3CN (0.056 g, 0.897 mmol, 2.3 eq) was added. The reaction was adjusted to pH {tilde over ( )} 7 with HOAc. After stirring overnight the reaction was diluted with Et2O/water and the layers were separated. The organic layer was washed with saturated aqueous NaHCO3 (×2), water (×3), brine (×1), and dried over Na2SO4. The inorganics were filtered off, and the solvent was removed in vacuo. Purification via flash chromatography yielded 0.0638 g (0.228 mmol, 58% yield) of tert-butyl 3-(dimethylamino)-5-methoxybenzylcarbamate.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with saturated aqueous NaHCO3 (×2), water (×3), brine (×1)
  3. dry with materialdried over Na2SO4
  4. filtrationThe inorganics were filtered off
  5. customthe solvent was removed in vacuo
  6. customPurification via flash chromatography

Sources & evidence

ORD record
ord-5c8e029804c74ae8a4faf5fa089f3ae5
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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