Diisopropyl Ether → HCID 9884753, compound

HRID 1953240Notes

Reaction equation

HRID 1953240 reaction equation
C[CH:2]([C:13]([CH:15]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)C)=O)C1C=CC(OC)=C(OC)C=1.[NH2:27][CH2:28][C@@H:29]([C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=1)[OH:30].C(OC(C)C)(C)C>[Pt]=O.C(O)(C)C>[Cl:37][C:33]1[CH:32]=[C:31]([C@@H:29]([OH:30])[CH2:28][NH:27][C@H:13]([CH3:2])[CH2:15][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=2)[CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 7914Diisopropyl EtherHCID 9920489(R)-2-Amino-1-(3-chlorophenyl)ethanolHCID 54132785HCID 54132785, compound

Product 1

HCID 9884753HCID 9884753, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 3776IsopropanolSolvent

Procedure

To a mixture of 5.83 g of methyl-3,4-dimethoxyphenylmethyl ketone, 5.15 g of (R)-2-amino-1-(3-chlorophenyl)ethanol and 50 mg of platinum oxide were added 15 ml of isopropyl alcohol and 30 ml of diisopropyl ether, and the reducing reaction was carried out at room temperature, at 1 atm under hydrogen atmosphere for 24 hours. After removing off platinum oxide by filtration, the solvent was distilled off under reduced pressure to give 6.51 g of white oil of (R,R)-1-(3-chlorophenyl)-2-[[2-(3,4-dimethoxyphenyl)-1-methylethyl]amino]ethanol (yield 62%). The optical purity of the (R,R)-isomer was 65%.

Workup

  1. customthe reducing reaction
  2. customAfter removing off platinum oxide
  3. filtrationby filtration
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-438f062a99754dccb05e4e7e0c58a177
Source dataset
uspto-grants-2000_09
Patent number
US06114582

Reaction notes

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