Potassium sodium tartarate → (2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-formylpyrrolidine

HRID 2073253

반응식

HRID 2073253 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][C@H:9]1[C:24](OC)=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([NH:13][S:14]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)(=[O:15])=[O:16])[CH2:10][C@H:9]1[CH:24]=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 3

HCID 9855836Potassium sodium tartarateHCID 14772685(2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-methoxycarbonylpyrrolidineHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 15670377(2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-formylpyrrolidine수율 65.9%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of (2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-methoxycarbonylpyrrolidine (9.01 g) in toluene (70 ml) was added dropwise 1.5 molar solution of diisobutylaluminum hydride (61.2 m mol) in tetrahydrofuran (40.8 ml) at -78° C. After the mixture was stirred at -78° C. for 1.5 hours, saturated aqueous potassium sodium tartrate was added to the reaction mixture and the mixture was filtered through Celite. The solid was washed with ethyl acetate and the combined organic solution was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column with a mixture of ethyl acetate and n-hexane (1:2-2:1) as an eluent to give (2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-formylpyrrolidine (5.51 g) as pale yellow crystal.

후처리

  1. filtrationthe mixture was filtered through Celite
  2. washThe solid was washed with ethyl acetate
  3. washthe combined organic solution was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was chromatographed on a silica gel column with a mixture of ethyl acetate and n-hexane (1:2-2:1) as an eluent

출처 및 근거

ORD 기록
ord-1615f33cf72341f1b70f465910f68ced
출처 데이터셋
uspto-grants-1990_04
특허 번호
US04916152

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