Ammonium Chloride → HCID 15289535、化合物

HRID 2211405ノート

反応式

HRID 2211405 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-butoxycarbonyl-perhydroisoindol-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 and then treated with 250 cm3 of an aqueous saturated solution of ammonium chloride, diluted with 200 cm3 of ethyl acetate, washed with 200 cm3 of water (twice) and then with 200 cm3 of an aqueous saturated solution of sodium chloride, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed over 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-butoxycarbonyl-perhydroisoindol-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 an aqueous saturated solution of sodium chloride
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is chromatographed over 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-2fe6d72228814e09a54bcbcb4effd3df
出典データセット
uspto-grants-1995_10
特許番号
US05463077

反応ノート

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