Ammonium Chloride → (3aR,5S,6aR)-2,2-dimethyl-5-[(2R)-oxiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole

HRID 60696노트

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HRID 60696 반응식
CC1C=CC(S(O[CH2:12][C@H:13]([C@H:15]2[O:24][C@@H:18]3[O:19][C:20]([CH3:23])([CH3:22])[O:21][C@@H:17]3[CH2:16]2)[OH:14])(=O)=O)=CC=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[NH4+].[Cl-]>C1COCC1>[CH3:22][C:20]1([CH3:23])[O:19][C@H:18]2[O:24][C@H:15]([C@H:13]3[CH2:12][O:14]3)[CH2:16][C@H:17]2[O:21]1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 15473566[(2R)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxy-ethyl] 4-methylbenzenesulfonate2회

생성물 1

HCID 10910249(3aR,5S,6aR)-2,2-dimethyl-5-[(2R)-oxiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole수율 77.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-70 °C

실험 절차

To a solution of [(2R)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxy-ethyl] 4-methylbenzenesulfonate (compound 6a, 100 g, 280 mmol) in anhydrous THF (1500 mL) cooled at −70° C. was added potassium bis(trimethylsilyl)amide (340 mL, 340 mmol, 1 M in THF) under N2 atmosphere. After being stirred at −70° C. for 1 hour, the reaction mixture was poured into saturated NH4Cl solution. The organic layer was separated and the aqueous phase was extracted with EtOAc. The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 1:3 EtOAc in petroleum ether) to afford 40.5 g of (3aR,5S,6aR)-2,2-dimethyl-5-[(2R)-oxiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole (compound 6b) as a slight yellow oil.

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (eluting with 1:3 EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-0bac61f13d1a47729c73cbeecbe5f4b7
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09441008B2

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