Methanol → Ethanone, 2-(diethylamino)-1-phenyl-

HRID 1638417Notes

Reaction equation

HRID 1638417 reaction equation
Cl.[CH2:2]([N:4]([CH2:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])[CH2:5][CH3:6])[CH3:3].CO.Cl.C(N(CC)CC(C1C=CC=CC=1)O)C.O>[H][H]>[CH2:2]([N:4]([CH2:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9])[CH2:5][CH3:6])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 19842493HCID 19842493, compoundHCID 198425062-(Diethylamino)-1-phenylethan-1-one--hydrogen chloride (1/1)

Product 1

HCID 417945Ethanone, 2-(diethylamino)-1-phenyl-Yield 95%

Reagents, catalysts & solvents 1

HCID 178418361HCID 178418361, compoundSolvent

Procedure

To 1.59 g (7 m-mol) of N,N-diethylphenacylamine hydrochloride were added 10 ml of methanol, 1.7 mg (0.0035 m-mol) of rhodium 1,5-cyclooctadiene chloride complex and 5.3 mg (0.0091 m-mol) of (2S,4S)-N-phenoxycarbonyl-4-dicyclohexylphosphino-2-iphenylphosphinomethylpyrrolidine (PCPM). The mixture was charged into an autoclave and stirred for 20 hours at 50° C. in hydrogen atmosphere at a pressure of 5 atm. It was confirmed by TLC that 100% of the starting material had been converted. An after-treatment was carried out in the same manner as in Example 30 whereby 1.50 g of N,N-diethyl-2-amino-1-phenylethanol hydrochloride was obtained. [α]D23 =+61.1° (c=5, water) (optical yield: 95% ee).

Workup

  1. additionThe mixture was charged into an autoclave
  2. customwas obtained

Sources & evidence

ORD record
ord-3b5ad6ef02f94e28b2345f975f241808
Source dataset
uspto-grants-1989_11
Patent number
US04879389

Reaction notes

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