Hydrochloric Acid → ((2R,4S)-1-[(4-Methylphenyl)sulfonyl]-4-{[(4-methylphenyl)sulfonyl]oxy}pyrrolidinyl)methyl 4-methylbenzenesulfonate

HRID 906219ノート

反応式

HRID 906219 の反応式
[OH:1][CH2:2][C@@H:3]1[N:7]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:6][C@@H:5]([OH:18])[CH2:4]1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.Cl>N1C=CC=CC=1>[C:14]1([CH3:17])[CH:15]=[CH:16][C:11]([S:8]([N:7]2[CH2:6][C@@H:5]([O:18][S:25]([C:22]3[CH:23]=[CH:24][C:19]([CH3:29])=[CH:20][CH:21]=3)(=[O:27])=[O:26])[CH2:4][C@@H:3]2[CH2:2][O:1][S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])(=[O:10])=[O:9])=[CH:12][CH:13]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 15629267(3S,5R)-5-Hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol

生成物 1

HCID 15629272((2R,4S)-1-[(4-Methylphenyl)sulfonyl]-4-{[(4-methylphenyl)sulfonyl]oxy}pyrrolidinyl)methyl 4-methylbenzenesulfonate

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
10 °C

実験手順

To an ice-cold solution of 5-hydroxymethyl-1-(toluene-4-sulfonyl)-pyrrolidin-3-ol (4) (0.45 g, 1.66 mmol) in pyridine (3 mL) is added 4-toluylsulfonyl chloride (1.11 g, 5.81 mmol) in one portion. The temperature rises to 50° C., then the reaction mixture is cooled to 10° C., kept at that temperature for an additional 2 h and then left at room temperature overnight. The mixture is poured into 2N HCl (13 mL). On cooling the compound precipitates out and separated by filtration, washed with cold water (2×5 mL), and dried under reduced pressure to give compound (5) as white solid.

後処理

  1. customrises to 50° C.
  2. waitleft at room temperature overnight
  3. temperatureOn cooling the compound
  4. customprecipitates out and
  5. customseparated by filtration
  6. washwashed with cold water (2×5 mL)
  7. customdried under reduced pressure

出典と根拠

ORDレコード
ord-88df640c4e7b431ab4c2a3fde45bbe14
出典データセット
uspto-grants-2011_09
特許番号
US08012983B2

反応ノート

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