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

HRID 2392765노트

반응식

HRID 2392765 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 1140Toluene용매3회HCID 8857Ethyl Acetate용매HCID 19096565Water ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-006a28724511403588bbf081054c83c1
출처 데이터셋
uspto-grants-1998_09
특허 번호
US05801201

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