Water → cis-l-Tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine

HRID 344290노트

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HRID 344290 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH:10]([OH:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:24][S:25](Cl)(=[O:27])=[O:26].O>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][O:15][S:25]([CH3:24])(=[O:27])=[O:26])[C@H:10]([OH:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3].[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH2:14][O:15][S:25]([CH3:24])(=[O:27])=[O:26])[C@H:10]([OH:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 154810601,1-Dimethylethyl 3-hydroxy-4-(hydroxymethyl)-1-piperidinecarboxylate

생성물 2

HCID 86753635cis-l-Tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidineHCID 86753636trans-1-Tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-tert-butoxycarbonyl-3-hydroxy-4-hydroxymethylpiperidine (6.5 g) and triethylamine (5.87 ml) in dichloromethane (100 ml) was added dropwise methanesulfonyl chloride (3.54 g) under ice-cooling, and the resulting mixture was stirred at room temperature for 6 hr. Water was added to the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with brine and dried. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (chloroform:methanol=40:1) to give 4.44 g of cis-l-tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine and 0.93 g of trans-1-tert-butoxycarbonyl-3-hydroxy-4-methanesulfonyloxymethylpiperidine.

후처리

  1. temperaturecooling
  2. extractionthe mixture was extracted with chloroform
  3. washThe organic layer was washed with brine
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (chloroform:methanol=40:1)

출처 및 근거

ORD 기록
ord-cb436ae2cbc1490ba74c7a83af05b90a
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05864039

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