Acetic Acid → HCID 17932759, compound

HRID 2253045Notes

Reaction equation

HRID 2253045 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[C:11]1([CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl.CCCCCC>[C:11]1([CH:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:18][NH:8][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 13696DiphenylacetaldehydeHCID 754524-MethoxybenzylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 17932759HCID 17932759, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

To a stirring solution of 4-methoxybenzylamine (1.4 g, 0.010 mole) and 2,2-diphenylacetaldehyde (2.0 g, 0.010 mole) in dichloromethane (50 mL) was added sodium triacetoxyborohydride (2.38 g, 0.011 mole) and acetic acid (2.0 mL). The reaction mixture was stirred overnight. The reaction mixture was concentrated and the residue was dissolved in EtOAc. The EtOAc solution was washed with saturated aqueous NaHCO3. The organic extracts were dried over Na2SO4, filtered, and concentrated. The crude mixture was subjected to column chromatography over silica gel (silica gel 60, EM Science) using 30% EtOAc: Hexane as eluent to afford 1.75 g (54% yield) of the title compound as a yellow oil. MS (ESI) 318.0 (M+H+).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe EtOAc solution was washed with saturated aqueous NaHCO3
  4. dry with materialThe organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4a754acfb361480bb43b1abdfc226883
Source dataset
uspto-grants-2008_01
Patent number
US07323494B2

Reaction notes

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