Ammonium Chloride → HCID 121396363、化合物

HRID 60697ノート

反応式

HRID 60697 の反応式
[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

参加物

6

反応物 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]dioxole2 回HCID 178418573HCID 178418573、化合物

生成物 1

HCID 121396363HCID 121396363、化合物収率 75.5%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e0ce30c523b2417cade7f8e5c4933e00
出典データセット
uspto-grants-2016_09
特許番号
US09441008B2

反応ノート

読み込み中…