Ammonium Chloride → HCID 15289535、化合物

HRID 375432ノート

反応式

HRID 375432 の反応式
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:9]1([C:15]2([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:23]3[C@@H:19]([CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22]3)[C:18](=[O:31])[CH2:17][CH2:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Cl-].[NH4+]>C(OCC)C.O1CCCC1.C(OCC)(=O)C>[C:1]1([C@:18]2([OH:31])[CH2:17][CH2:16][C:15]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C@@H:23]3[C@H:19]2[CH2:20][N:21]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH2:22]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 3

HCID 25517Ammonium ChlorideHCID 53854262HCID 53854262、化合物HCID 178418255HCID 178418255、化合物

生成物 1

HCID 15289535HCID 15289535、化合物収率 41.1%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A suspension of 10.78 g of phenylmagnesium bromide in 65 cm3 of diethyl ether is added dropwise to a solution of 11.66 g of (3aS,7aS)-7,7-diphenyl-2-tert-butoxycarbonylperhydroisoindol-4-one in 70 cm3 of dry tetrahydrofuran at room temperature, while stirring. The reaction mixture is stirred at room temperature for 24 hours, refluxed for 5 hours, subsequently treated with 250 cm3 of a saturated aqueous solution of ammonium chloride, diluted with 200 cm3 of ethyl acetate, washed with 200 cm3 of water (twice) and then with 200 cm3 of a saturated aqueous solution of sodium chloride, and is dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 5.3 cm, height 31.5 cm) by eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (90/10 by volume) and collecting fractions of 100 cm3. Fractions 23 to 48 are combined and concentrated to dryness under reduced pressure (2.7 kPa). 5.75 g of (3aS,4S,7aS)-4,7,7-triphenyl-2-tert-butoxycarbonylperhydroisoindol-4-ol are obtained in the form of a pale yellow foam.

後処理

  1. stirringThe reaction mixture is stirred at room temperature for 24 hours
  2. temperaturerefluxed for 5 hours
  3. washwashed with 200 cm3 of water (twice) and then with 200 cm3 of a saturated aqueous solution of sodium chloride
  4. dry with materialis dried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is chromatographed on a Merck silica gel column (particle size 0.04-0.06 mm, diameter 5.3 cm, height 31.5 cm)
  8. washby eluting under a pressure of 0.5 bar of nitrogen with a mixture of cyclohexane and ethyl acetate (90/10 by volume)
  9. customcollecting fractions of 100 cm3
  10. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

出典と根拠

ORDレコード
ord-cd6cc7a81d484f10b9df5e5d76f1388f
出典データセット
uspto-grants-1996_01
特許番号
US05484804

反応ノート

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