4-Toluenesulfonyl chloride → ((1R,2S)-2-hydroxycyclohexyl)methyl 4-methylbenzenesulfonate

HRID 875573ノート

反応式

HRID 875573 の反応式
[OH:1][CH2:2][C@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]1[OH:9].[C:10]1([CH3:20])[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:20][C:10]1[CH:15]=[CH:14][C:13]([S:16]([O:1][CH2:2][C@H:3]2[CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]2[OH:9])(=[O:18])=[O:17])=[CH:12][CH:11]=1

参加物

5

反応物 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 1514322(1S,2R)-2-(hydroxymethyl)cyclohexanol

生成物 1

HCID 14970968((1R,2S)-2-hydroxycyclohexyl)methyl 4-methylbenzenesulfonate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (1S,2R)-2-(hydroxymethyl)cyclohexanol (0.44 g, 3.85 mmol) and N,N-dimethylaminopyridine (DMAP) (0.485 g, 3.97 mmol) in anhydrous CH2Cl2 (10 mL) was added a solution of p-toluenesulfonyl chloride (0.767 g, 4.02 mmol) in anhydrous CH2Cl2 (5 mL) under argon at room temperature. The reaction mixture was stirred at room temperature for 22 hrs and triethylamine (0.5 mL) was added. The mixture was stirred for additional 100 min, concentrated under reduced pressure, water was added and the product was extracted with EtOAc twice. Combined organic layers were washed with brine, concentrated under reduced pressure and purified by flash chromatography (20% to 70% EtOAc/hexanes gradient) to give ((1R,2S)-2-hydroxycyclohexyl)methyl 4-methylbenzenesulfonate as a colorless oil. Yield (0.732 g, 71%). 1H NMR (400 MHz, DMSO-d6) δ 7.72-7.76 (m, 2H), 7.42-7.47 (m, 2H), 4.60 (d, J=5.5 Hz, 1H), 4.12 (dd, J=3.1, 9.2 Hz, 1H), 3.90 (dd, J=7.2, 9.2 Hz, 1H), 3.00-3.10 (m, 1H), 2.40 (s, 3H), 1.73-1.80 (m, 1H), 1.46-1.65 (m, 3H), 1.34-1.42 (m, 1H), 0.85-1.16 (m, 4H).

後処理

  1. stirringThe mixture was stirred for additional 100 min
  2. concentrationconcentrated under reduced pressure, water
  3. additionwas added
  4. extractionthe product was extracted with EtOAc twice
  5. washCombined organic layers were washed with brine
  6. concentrationconcentrated under reduced pressure
  7. custompurified by flash chromatography (20% to 70% EtOAc/hexanes gradient)

出典と根拠

ORDレコード
ord-58c33ea009774a5e81bb5ce48e41568c
出典データセット
uspto-grants-2015_03
特許番号
US08981153B2

反応ノート

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