Sulfoxonium, trimethyl-, iodide (1:1) → tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

HRID 854329

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HRID 854329 반응식
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[I-].[CH3:16][S+](C)(C)=O.CC(C)([O-])C.[Na+]>C1COCC1.COCCOC>[O:1]1[C:2]2([CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH2:16]1

참가 물질

5

반응물 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 23676156Sodium t-butoxide

생성물 1

HCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

시약·촉매·용매 1

HCID 22732251Tetrahydrofuran dimethoxyethane용매

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온도
60 °C

실험 절차

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (0.50 g, 2.51 mmol) in THF/DME (2:1, 6 mL) at 60° C. was added trimethylsulfoxonium iodide (0.58 g, 2.63 mmol) and sodium t-butoxide (0.25 g, 2.63 mmol). The reaction mixture was stirred at 60° C. for 30 min, cooled to rt and concentrated. Water was added and the mixture was extract with EtOAc twice. The combined organics were dried over Na2SO4, filtered and concentrated. Purification on silica gel (3:1, hexanes:EtOAc) gave tert-butyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate as a clear oil that solidified upon standing.

후처리

  1. temperaturecooled to rt
  2. concentrationconcentrated
  3. additionWater was added
  4. extractionthe mixture was extract with EtOAc twice
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification on silica gel (3:1, hexanes:EtOAc)

출처 및 근거

ORD 기록
ord-cae21a44277c4849a0103731f1b91da8
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259157B2

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