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

HRID 2392765ノート

反応式

HRID 2392765 の反応式
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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒3 回HCID 8857Ethyl Acetate溶媒HCID 19096565Water ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-006a28724511403588bbf081054c83c1
出典データセット
uspto-grants-1998_09
特許番号
US05801201

反応ノート

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