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Boron tribromide → 1-(2-hydroxy-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

HRID 323367
ノート
印刷プレビュー

反応式

HRID 323367 の反応式
C[O:2][C:3]1[CH:24]=[CH:23][C:22]([N:25]2[CH:29]=[N:28][N:27]=[N:26]2)=[CH:21][C:4]=1[C:5]([N:7]1[CH2:11][CH2:10][C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([CH2:12][CH2:13][OH:14])[CH2:8]1)=[O:6].B(Br)(Br)Br.CO.ClCCl.C1(C)C=CC=CC=1.CO>ClCCl>[OH:2][C:3]1[CH:24]=[CH:23][C:22]([N:25]2[CH:29]=[N:28][N:27]=[N:26]2)=[CH:21][C:4]=1[C:5]([N:7]1[CH2:11][CH2:10][C:9]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([CH2:12][CH2:13][OH:14])[CH2:8]1)=[O:6]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 25134Boron tribromideHCID 184644561-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidineHCID 21226129Dichloromethane methanolHCID 21867641Toluene methanol

生成物 1

HCID 184650361-(2-hydroxy-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒
2 回

実験手順

Combine 1-(2-methoxy-5-(1H-tetrazol-1-yl)benzoyl)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (prepared from (−)-3-phenyl-3-(2-hydroxyethyl)pyrrolidine (R,R)-di-p-anisoyltartaric acid salt) (2.0 g, 5.1 mmol) and anhydrous dichloromethane (100 mL). Cool in an ice bath. Add a solution of boron tribromide (17.8 mL, 1 M, 17.8 mmol) and stir. After 2 hours, pour the reaction mixture into ice-water and stir vigorously. After 18 hours, separate the layers and extract the organic layer with water. Saturate the aqueous layer with sodium chloride and extract with dichloromethane. Combine the organic layers, dry over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 5% methanol/dichloromethane/0.5% concentrated aqueous ammonia to give a residue. Combine the residue and toluene/methanol. Evaporate invacao to give a residue, dissolve in dichloromethane, filter, evaporate, combine with dichloromethane, again evaporate to remove residual toluene to give the title compound: mp; 86-96° C. Rf=0.37 (silica gel, 5% methanol/dichloromethane/0.5% concentrated aqueous ammonia).

後処理

  1. temperatureCool in an ice bath
  2. stirringstir vigorously
  3. waitAfter 18 hours
  4. customseparate the layers
  5. extractionextract the organic layer with water
  6. concentrationSaturate the aqueous layer with sodium chloride
  7. extractionextract with dichloromethane
  8. dry with materialdry over Na2SO4
  9. filtrationfilter
  10. customevaporate in vacuo
  11. customto give a residue
  12. customEvaporate invacao
  13. customto give a residue
  14. filtrationfilter
  15. customevaporate
  16. customagain evaporate
  17. customto remove residual toluene

出典と根拠

ORDレコード
ord-2c6da1d73a1d4f7bb93d57cefe0e7557
出典データセット
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06211199B1

反応ノート

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