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Hydrogen Peroxide → (1R,3R)-methyl 1-(benzyloxycarbonylamino)-3-(4-(2-hydroxyethyl)phenyl)cyclopentanecarboxylate

HRID 1511866
ノート
印刷プレビュー

反応式

HRID 1511866 の反応式
B1C2CCCC1CCC2.[CH2:10]([O:17][C:18]([NH:20][C@:21]1([C:34]([O:36][CH3:37])=[O:35])[CH2:25][CH2:24][C@@H:23]([C:26]2[CH:31]=[CH:30][C:29]([CH:32]=[CH2:33])=[CH:28][CH:27]=2)[CH2:22]1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.B([O-])[O-:39].[OH-].[Na+].OO>C1COCC1>[CH2:10]([O:17][C:18]([NH:20][C@:21]1([C:34]([O:36][CH3:37])=[O:35])[CH2:25][CH2:24][C@@H:23]([C:26]2[CH:27]=[CH:28][C:29]([CH2:32][CH2:33][OH:39])=[CH:30][CH:31]=2)[CH2:22]1)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 57554635(1R,3R)-methyl 1-(benzyloxycarbonylamino)-3-(4-vinylphenyl)cyclopentanecarboxylateHCID 178514824HCID 178514824、化合物

生成物 1

HCID 57554629(1R,3R)-methyl 1-(benzyloxycarbonylamino)-3-(4-(2-hydroxyethyl)phenyl)cyclopentanecarboxylate
収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

9-BBN (25 ml, 12.50 mmol) was added dropwise to a stirred and cooled solution of (1R,3R)-methyl 1-(benzyloxycarbonylamino)-3-(4-vinylphenyl)cyclopentanecarboxylate (0.682 g, 1.797 mmol) in THF (15 mL). The reaction mixture was checked by TLC to ensure complete conversion to boronate. Once complete the ice bath was removed and stirring was continued overnight. The reaction mixture was cooled to 0° C. and methanol (20 ml) was added. Aqueous NaOH (7.30 ml, 14.59 mmol) and H2O2 (1.522 ml, 14.90 mmol) were poured into the reaction mixture. Stirring was continued for 2 hours. The solvent was removed under reduced pressure and the product purified by FCC to afford (1R,3R)-methyl 1-(benzyloxycarbonylamino)-3-(4-(2-hydroxyethyl)phenyl)cyclopentanecarboxylate (0.507 g, 1.276 mmol, 71.0% yield) as colorless oil.

後処理

  1. customOnce complete the ice bath was removed
  2. stirringstirring
  3. additionmethanol (20 ml) was added
  4. stirringStirring
  5. waitwas continued for 2 hours
  6. customThe solvent was removed under reduced pressure
  7. customthe product purified by FCC

出典と根拠

ORDレコード
ord-9c2891a94cdb4a66bc71acb7475415ad
出典データセット
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08217027B2

反応ノート

読み込み中…

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