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Methanesulfonyl chloride → Ethyl N-tert-butoxycarbonyl-4-(3-methane-sulfonylaminobenzyl)piperidine-4-carboxylate

HRID 1068452
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HRID 1068452 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=2)([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:29][S:30](Cl)(=[O:32])=[O:31]>[Pd].C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][S:30]([CH3:29])(=[O:32])=[O:31])[CH:21]=2)([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 53931544ethyl N-tert-butoxycarbonyl-4-(3-nitrobenzyl)piperidine-4-carboxylate

생성물 1

HCID 21193321Ethyl N-tert-butoxycarbonyl-4-(3-methane-sulfonylaminobenzyl)piperidine-4-carboxylate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

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온도
60 °C

실험 절차

A mixture of ethyl N-tert-butoxycarbonyl-4-(3-nitrobenzyl)-piperidine-4-carboxylate (0.85 g, 2.17 mmol; Example 69, Step A) and 5% palladium on charcoal (0.06 g) in ethanol (100 mL) was hydrogenated at room temp. at 50 psi overnight. The resultant mixture was filtered through a plug of Celite, and the filtrate was concentrated under vacuum. The residue was dissolved in pyridine (5 mL), treated with methanesulfonyl chloride (0.24 mL, 3.2 mmol), and heated at 60° C. for 3 h. The product mixture was concentrated under vacuum, and the residue was subjected to column chromatography on silica gel eluting with 2% methanol in chloroform. Collection and concentration of appropriate fractions provided the title compound.

후처리

  1. customwas hydrogenated at room temp. at 50 psi overnight
  2. filtrationThe resultant mixture was filtered through a plug of Celite
  3. concentrationthe filtrate was concentrated under vacuum
  4. dissolutionThe residue was dissolved in pyridine (5 mL)
  5. concentrationThe product mixture was concentrated under vacuum
  6. customCollection and concentration of appropriate fractions

출처 및 근거

ORD 기록
ord-37216a9de38a4250be0ef2446c785eca
출처 데이터셋
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06248756B1

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