Hydrochloric Acid → (S)-3-(Toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 69513

反応式

HRID 69513 の反応式
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][C@H:21]([OH:24])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][C@H:21]([O:24][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylate

生成物 1

HCID 57957824(S)-3-(Toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a mixture of p-toluenesulfonyl chloride (10.0 g) in dry methylene chloride (40 mL) was added at 0° C. a solution of (S)-3-Hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (2.8 g) in dry methylene chloride (15 mL). DMAP (1.1 g) and triethylamine (6.1 g) was added. The mixture was stirred at 0° C. for 3 h. The reaction mixture was then allowed to reach room temperature and stirred for 12 h. The mixture was acidified with 1 N HCl. The organic layer was washed two times with 1 N HCl, one time with saturated sodium hydrogen carbonate solution and one time with brine. The organic layers were dried over sodium sulfate and concentrated. The product with the molecular weight of 341.43 (C16H23NO5S) was obtained in this way; MS (ESI): 342 (M+H+).

後処理

  1. customto reach room temperature
  2. stirringstirred for 12 h
  3. washThe organic layer was washed two times with 1 N HCl, one time with saturated sodium hydrogen carbonate solution and one time with brine
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe product with the molecular weight of 341.43 (C16H23NO5S) was obtained in this way

出典と根拠

ORDレコード
ord-d8cf54f57ee94f80a5892740a783cffd
出典データセット
uspto-grants-2014_09
特許番号
US08822495B2

関連ノート

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