Hydrochloric Acid → Benzyl 3-(2-aminocyclohexyl)-3-hydroxyazetidine-1-carboxylate

HRID 1717593ノート

反応式

HRID 1717593 の反応式
[OH:1][C:2]1([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][C:17]2=O)[CH2:5][N:4]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:3]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:29].[Na+].Cl>CO>[CH2:9]([O:8][C:6]([N:4]1[CH2:5][C:2]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[NH2:29])([OH:1])[CH2:3]1)=[O:7])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 67051703Benzyl 3-hydroxy-3-(2-oxocyclohexyl)azetidine-1-carboxylate

生成物 1

HCID 67051790Benzyl 3-(2-aminocyclohexyl)-3-hydroxyazetidine-1-carboxylate収率 73%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of benzyl 3-hydroxy-3-(2-oxocyclohexyl)azetidine-1-carboxylate (100 mg, 330 mmol) in methanol (1.60 mL) in the presence of ammonium acetate (191 mg, 2.48 mmol was cooled to 0° C. for 1 hour. Sodium cyanoborohydride (81.5 mg, 1.30 mmol) was added and the mixture was stirred at room temperature for 16 hours. To the reaction mixture was added 6 N hydrogen chloride (800 μL) and extracted with ethyl acetate. The aqueous layer was basified with aqueous sodium bicarbonate (pH 9) and extracted with dichloromethane. The combined organic portion was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford benzyl-3-(2-aminocyclohexyl)-3-hydroxyazetidine-1-carboxylate (73.7 mg, 73%). MS (EI) for C17H24N2O3: 305 (MH+).

後処理

  1. extractionextracted with ethyl acetate
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic portion was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-707132b338ba40ac9276d453e417d74b
出典データセット
uspto-grants-2010_09
特許番号
US07803839B2

反応ノート

読み込み中…