Water → cis-2-Triphenylmethylaminocyclohexanol

HRID 2399734ノート

反応式

HRID 2399734 の反応式
Cl.[NH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]1[OH:9].[C:10]1([C:16](Cl)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.O>C(Cl)Cl>[C:10]1([C:16]([NH:2][C@H:3]2[CH2:8][CH2:7][CH2:6][CH2:5][C@H:4]2[OH:9])([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

参加物

6

反応物 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 12228413(1R,2S)-2-aminocyclohexan-1-ol hydrochloride

生成物 1

HCID 54233547cis-2-Triphenylmethylaminocyclohexanol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of cis-2-aminocyclohexanol hydrochloride (4.88 g; 32 mmol) (William S. Johnson and Elliot N. Schubert, J.A.C.S., Vol. 72, pp. 2187-2190 (1950), triphenylmethylchloride (10.7 g; 38.4 mmol) and triethylamine (16 ml; 115 mmol) in 250 ml methylene chloride are refluxed for 3 hrs. then stirred at room temperature overnight. The mixture is poured into H2O and extracted with CH2Cl2 (200 ml), dried (Na2SO4) concentrated in vacuo and flash chromatographed using 9:1 7:1; hexane:EtOAc to obtain cis-2-triphenylmethylaminocyclohexanol which is used directly in the next step.

後処理

  1. extractionextracted with CH2Cl2 (200 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo and flash
  4. customchromatographed

出典と根拠

ORDレコード
ord-76b8b4c2cdec433c9a174a2e1b9b67bd
出典データセット
uspto-grants-1995_09
特許番号
US05451596

反応ノート

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