Propanal → HCID 57440704, compound

HRID 2102357Notes

Reaction equation

HRID 2102357 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][CH2:16][CH:17]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([O:26][CH3:27])[CH:20]=1)[OH:18].[CH:28](=O)[CH2:29][CH3:30].C(=O)(O)[O-].[Na+]>ClCCl.O.CO>[NH3:15].[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([CH:17]([OH:18])[CH2:16][NH:15][CH2:28][CH2:29][CH3:30])=[CH:20][C:21]=1[O:26][CH3:27]

Participants

9

Reactant 4

HCID 527PropanalHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 13900464HCID 13900464, compound

Product 2

HCID 222AmmoniaHCID 57440704HCID 57440704, compoundYield 87.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Sodium triacetoxyborohydride (1.25 g, 5.89 mmol) was added with care to a solution of 2-amino-1-(4-chloro-3-methoxy-phenyl)-ethanol (J. Med. Chem., 30(10), 1887, (1987)) (600 mg, 2,98 mmol) and propionaldehyde (0.22 mL, 2.96 mmol) in dichloromethane (10 mL), and the reaction mixture was stirred at room temperature for 1 hour. Sodium bicarbonate solution (sat. aq., 10 mL) was added dropwise and then the reaction mixture was diluted further with water (20 mL) and dichloromethane (20 mL). The aqueous layer was separated and re-extracted with dichloromethane (2×20 mL). The combined organic layers were dried over anhydrous magnesium sulphate, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica eluting with dichloromethane:methanol:0.880 ammonia (95:5:0.5 to 92:8:0.8) to yield the title compound as a solid (320 mg, 1.31 mmol, 44%). 1H NMR (CDCl3, 400 MHz) δ: 0.90 (t, 3H), 1.50 (q, 2H), 2.50-2.70 (m, 5H), 2.90 (dd, 1H), 3.80 (s, 3H), 4.65 (dd, 1H), 6.85 (d, 1H), 7.00 (1H, d), 7.30 (bd, 1H). LRMS (APCI): m/z 244 (MH+), 226 (MH+ less H2O).

Workup

  1. customThe aqueous layer was separated
  2. extractionre-extracted with dichloromethane (2×20 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography on silica eluting with dichloromethane

Sources & evidence

ORD record
ord-599417ac18ec4548b2729e8cc1d8a83e
Source dataset
uspto-grants-2009_08
Patent number
US07576081B2

Reaction notes

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