Hydrochloric Acid → HCID 15645976、化合物

HRID 1196877ノート

反応式

HRID 1196877 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][CH:13]2[CH:25]=O)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH:27]1[CH2:31][CH2:30][CH:29]([OH:32])[CH2:28]1.Cl.[Na].C([BH3-])#N>CO>[NH3:12].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:14][CH:13]2[CH2:25][N:27]2[CH2:31][CH2:30][CH:29]([OH:32])[CH2:28]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 982104-HydroxypyrrolidineHCID 156459541-[(3,4-Dichlorophenyl)acetyl]-4-(phenylmethyl)-2-piperazine carboxaldehydeHCID 131717404HCID 131717404、化合物

生成物 2

HCID 222AmmoniaHCID 15645976HCID 15645976、化合物収率 109.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A solution of the product of stage (ii) (3.67 g) in methanol (60 ml) was added to a stirred suspension of 3-pyrrolidinol (982 mg) and 3 Å molecular sieves (3.68 g) in methanol (35 ml), followed by adjustment of the pH to 6 using methanolic hydrogen chloride solution. Sodium-cyanoborohydride (1.30 g) was added portionwise and the resulting suspension was stirred under nitrogen for 19 h. The suspension was filtered and the filtrate evaporated to dryness. The residue was partitioned between aqueous 2N sodium carbonate solution (150 ml) and dichloromethane (100 ml) and the aqueous layer was further extracted with dichloromethane (2×50 ml)). The combined organic extracts were dried and evaporated to give an oil, which was purified by dry flash column chromatography on silica gel eluting with a mixture of dichloromethane:methanol:0.880 NH3 (200:8:1) to give the title compound as a foam (2.38 g).

後処理

  1. filtrationThe suspension was filtered
  2. customthe filtrate evaporated to dryness
  3. customThe residue was partitioned between aqueous 2N sodium carbonate solution (150 ml) and dichloromethane (100 ml)
  4. extractionthe aqueous layer was further extracted with dichloromethane (2×50 ml))
  5. customThe combined organic extracts were dried
  6. customevaporated
  7. customto give an oil, which
  8. customwas purified
  9. customby dry flash column chromatography on silica gel eluting
  10. additionwith a mixture of dichloromethane

出典と根拠

ORDレコード
ord-bb92b9268be5490e90dfd9b3c2a9cb20
出典データセット
uspto-grants-1992_05
特許番号
US05116842

反応ノート

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