HCID 18974552, compound → HCID 18974513, compound

HRID 2394984Notes

Reaction equation

HRID 2394984 reaction equation
Cl.[CH3:2][N:3]([CH3:18])[CH2:4][CH:5]([CH3:17])[C:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15]C)[CH:10]=1)([OH:8])[CH3:7].[Cl:19]CCl.[OH-].[Na+].[H-].C([Al+]CC(C)C)C(C)C>CCOCC>[ClH:19].[CH3:18][N:3]([CH3:2])[CH2:4][CH:5]([CH3:17])[C:6]([C:9]1[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=1)([OH:8])[CH3:7]

Participants

5

Reactant 3

HCID 18974552HCID 18974552, compoundHCID 21225700DiisobutylaluminumhydrideHCID 23721229Sodium hydroxide methylene chloride

Product 1

HCID 18974513HCID 18974513, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Starting from (RS)-3-dimethylamino-1-(3-methoxy-phenyl)-2-methyl-propan-1-one and methyl iodide, (2RS,3SR)-4-dimethylamino-2-(3-methoxy-phenyl)-3-methyl-butan-2-ol hydrochloride (23) was obtained, under the conditions given in Example 1 (1st step) and using ether as a solvent, in a yield of 46% and with a melting point of 178°-179° C. The base was released from (23) with dichloromethane/sodium hydroxide solution. After drying the solvent, the dichloromethane was distilled off under vacuum. 23.7 g (0.1 mole) of the base were reacted with diisobutylaluminium hydride as in Example 2. In this manner, 18.5 g (71% theoretical) of hydrochloride (22) were obtained with a melting point of 183°-184° C.

Workup

  1. customAfter drying the solvent
  2. distillationthe dichloromethane was distilled off under vacuum

Sources & evidence

ORD record
ord-d4898fb0859f41ff98d142f763f745c3
Source dataset
uspto-grants-1998_09
Patent number
US05811582

Reaction notes

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