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3-Aminoazetidine, 3-BOC protected → [1-(4-Benzo[1,3]dioxol-5-yl-cyclohex-3-enyl)-azetidin-3-yl]-carbamic acid tert-butyl ester

HRID 1893218
ノート
印刷プレビュー

反応式

HRID 1893218 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH2:15][CH2:14][C:13](=O)[CH2:12][CH:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[C:17]([O:21][C:22](=[O:28])[NH:23][CH:24]1[CH2:27][NH:26][CH2:25]1)([CH3:20])([CH3:19])[CH3:18].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:17]([O:21][C:22](=[O:28])[NH:23][CH:24]1[CH2:27][N:26]([CH:13]2[CH2:14][CH2:15][C:10]([C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)=[CH:11][CH2:12]2)[CH2:25]1)([CH3:20])([CH3:18])[CH3:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 15194053-Aminoazetidine, 3-BOC protectedHCID 5049666Sodium triacetoxyborohydrideHCID 595419144-(Benzo[D][1,3]dioxol-5-YL)cyclohex-3-enone

生成物 1

HCID 59541968[1-(4-Benzo[1,3]dioxol-5-yl-cyclohex-3-enyl)-azetidin-3-yl]-carbamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 4-benzo[1,3]dioxol-5-yl-cyclohex-3-enone (as prepared in the previous step, 680 mg, 3.15 mmol) and azetidin-3-yl-carbamic acid tert-butyl ester (BetaPharma, 542 mg, 3.15 mmol) in DCM (10 mL) was treated with NaBH(OAc)3 (Aldrich, 2.0 g, 9.45 mmol) at room temperature. The reaction was stirred for 4 hours and quenched with saturated sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted 3 times with DCM. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give the crude product, which was then purified by a CombiFlash® system using hexanes and ethyl acetate as eluent (from pure hexanes to pure ethyl acetate) to afford the title compound as a white solid.

後処理

  1. customquenched with saturated sodium bicarbonate
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted 3 times with DCM
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas then purified by a CombiFlash® system

出典と根拠

ORDレコード
ord-39770de8faf24be186483d6f207fced0
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08513229B2

反応ノート

読み込み中…

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