Acetic Acid → STK291283

HRID 1093036Notes

Reaction equation

HRID 1093036 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].C(O)(=O)C.[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 118072-Amino-2-methyl-1-propanolHCID 312444-MethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 272308STK291283Yield 61%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-amino-2-methyl-1-propanol (8.4, 94 mmol) in 1,2-dichloroethane (150 mL) and acetic acid (4.3 mL, 77 mmol) was added 4-methoxy benzaldehyde (11.5 mL, 94 mmol). After stirring for 10 min, sodium triacetoxyborohydride (49.9 g, 235.5 mmol) was added portion-wise over 20 min. The resulting mixture was stirred at 60° C. for 2 h then cooled to room temperature and quenched with saturated NaHCO3. The aqueous layer was washed with dichloromethane and made basic by the addition of 10N NaOH. The product was extracted with ethyl acetate, concentrated and crystallized from Et2O/hexane to give the title compound as a white solid (11.95 g, 61% yield). 1H NMR (300 MHz, CDCl3) δ: 7.32-7.20 (2H, m), 6.86-6.80 (2H, m), 3.76 (3H, s), 3.58 (2H, s), 3.30 (2H, s), 1.11 (6H, s). LCMS (M+H) calcd for C12H20NO2: 210.14; found: 210.20.

Workup

  1. stirringThe resulting mixture was stirred at 60° C. for 2 h
  2. customquenched with saturated NaHCO3
  3. washThe aqueous layer was washed with dichloromethane
  4. additionmade basic by the addition of 10N NaOH
  5. extractionThe product was extracted with ethyl acetate
  6. concentrationconcentrated
  7. customcrystallized from Et2O/hexane

Sources & evidence

ORD record
ord-15492ee3a1ef4a34a21f49d5e08ee9ea
Source dataset
uspto-grants-2012_03
Patent number
US08129398B2

Reaction notes

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