Ammonium Chloride → HCID 121396363, 화합물

HRID 60697노트

반응식

HRID 60697 반응식
[CH3:1][Mg]Br.[CH3:4][C:5]1([CH3:16])[O:9][C@H:8]2[O:10][C@H:11]([C@H:13]3[CH2:15][O:14]3)[CH2:12][C@H:7]2[O:6]1.[NH4+].[Cl-]>C1COCC1.[Cu]I>[CH3:4][C:5]1([CH3:16])[O:9][C@H:8]2[O:10][C@H:11]([C@H:13]([OH:14])[CH2:15][CH3:1])[CH2:12][C@H:7]2[O:6]1

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 10910249(3aR,5S,6aR)-2,2-dimethyl-5-[(2R)-oxiran-2-yl]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole2회HCID 178418573HCID 178418573, 화합물

생성물 1

HCID 121396363HCID 121396363, 화합물수율 75.5%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of CuI (19.3 g, 107 mmol) in dry THF (2000 mL) under N2 atmosphere was added methyl magnesium bromide (3 M in diethyl ether, 537 mL, 1.61 mol) at −70° C. After being stirred at this temperature for 1 hour, a solution 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, 100 g, 537 mmol, dissolved in anhydrous THF 200 mL) was added to reaction mixture dropwise. After being stirred at −70° C. for additional 2 hours, the reaction mixture was poured into saturated NH4Cl solution. The organic layer was separated and the aqueous phase was extracted with EtOAc twice. 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 82 g of (1R)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]propan-1-ol (compound 6c) as a slight yellow solid.

후처리

  1. stirringAfter being stirred at −70° C. for additional 2 hours
  2. customThe organic layer was separated
  3. extractionthe aqueous phase was extracted with EtOAc twice
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel (eluting with 1:3 EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-e0ce30c523b2417cade7f8e5c4933e00
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09441008B2

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