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Sodium Iodide → (2S,4R)-2-benzylsulfanylmethyl-1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine

HRID 1006787
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HRID 1006787 반응식
[CH3:1][S:2]([N:5]1[CH2:9][C@H:8]([S:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH2:7][C@H:6]1[CH2:20]OS(C)(=O)=O)(=[O:4])=[O:3].[Na+].[I-].[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[CH2:11]([S:10][CH2:20][C@@H:6]1[CH2:7][C@@H:8]([S:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[CH2:9][N:5]1[S:2]([CH3:1])(=[O:3])=[O:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
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반응물 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 87831882(2S,4R)-methanesulfonic acid 1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidin-2-ylmethyl ester

생성물 1

HCID 69430272(2S,4R)-2-benzylsulfanylmethyl-1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine수율 98.9%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A slurry of 300 mg (0.73 mmol) (2S,4R)-methanesulfonic acid 1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidin-2-ylmethyl ester and 109 mg (0.73 mmol) of NaI in 3 ml DMF at 0° C. was treated with 0.35 ml (2.93 mmol) benzylmercaptane and 96 mg (2.2 mmol) 55% NaH. The reaction was warmed up during 2 h to room temperature: and worked up with aqueous saturated NH4Cl solution/EtOAc (3×). The organic phase was dried over Na2SO4, evaporated and purified by crystallization (Et2O) to give 158 mg (49%) of (2S,4R)-2-benzylsulfanylmethyl-1-methanesulfonyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine, mp 69-71° C., MS: 438 (MH+).

후처리

  1. temperatureThe reaction was warmed up during 2 h to room temperature
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated
  4. custompurified by crystallization (Et2O)

출처 및 근거

ORD 기록
ord-74a0211184e3454aa4806ead42885db2
출처 데이터셋
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06790860B2

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