Ethanol → (1RS,2RS,4SR)-3-[4-(2-cyclopentyl-ethyl)-2-dimethylaminomethyl-1-hydroxy-cyclohexyl]-phenol hydrochloride

HRID 2392765Notes

Reaction equation

HRID 2392765 reaction equation
Cl.[CH:2]1([CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C)[CH:17]=3)([OH:15])[CH:11]([CH2:24][N:25]([CH3:27])[CH3:26])[CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[H-].C([Al+]CC(C)C)C(C)C.C(O)C.C[Si](C)(C)[Cl:43].O>C1(C)C=CC=CC=1.C(OCC)(=O)C.C(O)C.O>[ClH:43].[CH:2]1([CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][C:12]([C:16]3[CH:17]=[C:18]([OH:22])[CH:19]=[CH:20][CH:21]=3)([OH:15])[CH:11]([CH2:24][N:25]([CH3:27])[CH3:26])[CH2:10]2)[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 702EthanolHCID 21225700DiisobutylaluminumhydrideHCID 67641018(1RS,2RS,4SR)-4-(cyclopentyl-ethyl)-2-dimethylaminomethyl-1-(3-methoxyphenyl)-cyclohexanol hydrochlorideHCID 86753056Chlorotrimethylsilane water

Product 1

HCID 18980467(1RS,2RS,4SR)-3-[4-(2-cyclopentyl-ethyl)-2-dimethylaminomethyl-1-hydroxy-cyclohexyl]-phenol hydrochloride

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent3×HCID 8857Ethyl AcetateSolventHCID 19096565Water ethanolSolvent

Procedure

The reaction was conducted in a nitrogen atmosphere with the exclusion of moisture. 1.44 g (4 mmole) of the base of compound (52) were dissolved in 15 ml toluene. 25 ml of 20% diisobutylaluminium hydride in toluene (35 mmole) were added drop-wise with stirring. The mixture was subsequently boiled for 6.5 hours under reflux and was cooled. 5 ml ethanol, followed by 5 ml of 1:1 ethanol/water and 35 ml toluene, were added drop-wise at a temperature between 0° C. and 10° C. After stirring for one hour, the salts obtained were filtered off by suction and the solvent was removed by distillation. The oil obtained was then taken up in ethyl acetate. After adding trimethylchlorosilane/water, compound (57) was obtained in a yield of 0.35 g (23% theoretical).

Workup

  1. temperatureunder reflux
  2. temperaturewas cooled
  3. additionwere added drop-wise at a temperature between 0° C. and 10° C
  4. stirringAfter stirring for one hour
  5. customthe salts obtained
  6. filtrationwere filtered off by suction
  7. customthe solvent was removed by distillation
  8. customThe oil obtained

Sources & evidence

ORD record
ord-006a28724511403588bbf081054c83c1
Source dataset
uspto-grants-1998_09
Patent number
US05801201

Reaction notes

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