Acetic Acid → HCID 12050646, compound

HRID 1016594Notes

Reaction equation

HRID 1016594 reaction equation
Cl.CN.[CH2:4]([N:6](CC)CC)C.[CH3:11][C:12]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])[CH:13]=O.C(O)(=O)C.C([BH3-])#N.[Na+]>CO.C(OCC)(=O)C>[CH3:4][NH:6][CH2:13][C:12]([CH3:11])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochlorideHCID 11745716HCID 11745716, compound

Product 1

HCID 12050646HCID 12050646, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methylamine hydrochloride (500 mg, 7.41 mmol), triethylamine (1.00 mL, 725 mg, 7.17 mmol), and 3 Å molecular sieve pellets (1.05 g) were added to a stirred solution of 2,5-dimethyl-2-phenylhex-4-enal (500 mg, 2.47 mmol) in 5.0 mL of methanol at RT. After 1 h, the mixture was cooled in an ice bath and acetic acid (0.29 mL, 0.30 g, 5.1 mmol) was added followed by sodium cyanoborohydride (310 mg, 4.93 mmol). The mixture was allowed to slowly come to RT and stirred 16 h before being diluted with ethyl acetate (50 mL) and washed with saturated aqueous sodium bicarbonate (30 mL) and saturated aqueous sodium chloride (30 mL). The aqueous layers were extracted with ethyl acetate (30 mL) and the combined organic layers were dried over sodium sulfate and evaporated. The residue was purified by flash column chromatography on silica gel, eluting with 5% methanol in ethyl acetate to give 415 mg the title compound. 1H NMR (400 MHz, CD3OD): δ7.36-7.28 (m, 4H), 7.18 (t, 1H, J=7 Hz), 4.88 (t, 1H, J=7.5 Hz) 2.87 (d, 1H, J=12 Hz), 2.66 (d, 1H, J=12 Hz), 2.39 (dd, 1H, J=14, 7.5 Hz), 2.30 (dd, 1H, J=14, 8 Hz), 2.27 (s, 3H), 1.59 (s, 3H), 1.54 (s, 3H), 1.34 (s, 3H). Mass spectrum (NH3/CI): m/z=218 (M+1).

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. customto slowly come to RT
  3. washwashed with saturated aqueous sodium bicarbonate (30 mL) and saturated aqueous sodium chloride (30 mL)
  4. extractionThe aqueous layers were extracted with ethyl acetate (30 mL)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluting with 5% methanol in ethyl acetate

Sources & evidence

ORD record
ord-f87f41f5ce2542a29543e6772435375e
Source dataset
uspto-grants-2002_11
Patent number
US06476054B1

Reaction notes

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