4-Toluenesulfonyl chloride → Tert-butyl 3-(benzyloxy)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate

HRID 47327

반응식

HRID 47327 반응식
[CH2:1]([O:8][CH:9]([CH2:25]O)[CH2:10][C:11]1([OH:24])[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>N1C=CC=CC=1>[CH2:1]([O:8][CH:9]1[CH2:10][C:11]2([CH2:12][CH2:13][N:14]([C:17]([O:19][C:20]([CH3:22])([CH3:23])[CH3:21])=[O:18])[CH2:15][CH2:16]2)[O:24][CH2:25]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 73974-Toluenesulfonyl chloride2회HCID 22744648Tert-butyl 4-[2-(benzyloxy)-3-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylate

생성물 1

HCID 22744533Tert-butyl 3-(benzyloxy)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate수율 81.3%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

4.81 g of tert-butyl 4-[2-(benzyloxy)-3-hydroxypropyl]-4-hydroxy-1-piperidinecarboxylate was dissolved in 20 ml pyridine, 2.76 g of tosyl chloride was added thereto, and the mixture was stirred at room temperature for 2 hr. Further, 1.00 g of tosyl chloride was added thereto, and the mixture was stirred at room temperature for 30 min, and at 50° C. for 35 min. The reaction solution was partitioned into ethyl acetate and water, washed with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate and brine, and dried over magnesium sulfate. After filtration, the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give 3.72 g of tert-butyl 3-(benzyloxy)-1-oxa-8-azaspiro[4.5]decane-8-carboxylate.

후처리

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. waitat 50° C. for 35 min
  3. customThe reaction solution was partitioned into ethyl acetate and water
  4. washwashed with 1 N hydrochloric acid, saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated
  8. customthe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-e91f429d447a425abe1ada35ca2df06a
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699870B2

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