Hydrochloric Acid → (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-hydroxypyrrolidine

HRID 975647ノート

反応式

HRID 975647 の反応式
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si](C(C)(C)C)(C)C)[CH2:9][C@H:8]1[CH2:20][CH2:21][N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)=[O:6])[CH:2]=[CH2:3].Cl.C[O-].[Na+].CO.C(Cl)(Cl)Cl>CO>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH2:20][CH2:21][N:22]1[CH:26]=[CH:25][N:24]=[CH:23]1)=[O:6])[CH:2]=[CH2:3]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6212ChloroformHCID 23694274Sodium methanolate methanolHCID 54510818(2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-(t-butyldimethylsilyloxy)pyrrolidine

生成物 1

HCID 54134400(2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-hydroxypyrrolidine収率 118.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-(t-butyldimethylsilyloxy)pyrrolidine (11.11 g) in methanol (110 ml) was added conc. hydrochloric acid (7.32 ml) at ambient temperature with stirring and the solution was stirred at the same temperature for 2 hours. To a reaction solution was added 28% sodium methoxide-methanol solution (16.89 ml) under ice-cooling with stirring and the resulting insoluble material was filtered off. The filtrate was evaporated in vacuo to give a residue. To the residue was added chloroform. The organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo to give crude (2R,4R)-1-allyloxycarbonyl-2-[2-(imidazol-1-yl)ethyl]-4-hydroxypyrrolidine (9.19 g).

後処理

  1. stirringthe solution was stirred at the same temperature for 2 hours
  2. temperaturecooling
  3. stirringwith stirring
  4. filtrationthe resulting insoluble material was filtered off
  5. customThe filtrate was evaporated in vacuo
  6. customto give a residue
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-96c6739dafe340508cd0a5631c755766
出典データセット
uspto-grants-1997_03
特許番号
US05608056

反応ノート

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