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Dimethylamine → N,N-dimethyl-2-(1,4-dioxaspiro[4.5]decan-8-yl)acetamide

HRID 243566
ノート
印刷プレビュー

反応式

HRID 243566 の反応式
C[CH2:2][N:3](CC)[CH2:4]C.[CH3:8][N:9](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:10].[B-](F)(F)(F)F.[O:30]1[C:34]2([CH2:39][CH2:38][CH:37]([CH2:40][C:41]([OH:43])=O)[CH2:36][CH2:35]2)[O:33][CH2:32][CH2:31]1.CNC>CN(C=O)C.C1COCC1>[CH3:2][N:3]([CH3:4])[C:41](=[O:43])[CH2:40][CH:37]1[CH2:38][CH2:39][C:34]2([O:33][CH2:32][CH2:31][O:30]2)[CH2:35][CH2:36]1.[CH3:8][N:9]([CH3:10])[C:41](=[O:43])[CH2:40][CH:37]1[CH2:38][CH2:39][C:34](=[O:33])[CH2:35][CH2:36]1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 151011212-(1,4-Dioxaspiro(4.5)decan-8-yl)acetic acid

生成物 2

HCID 59442805N,N-dimethyl-2-(1,4-dioxaspiro[4.5]decan-8-yl)acetamideHCID 59442836N,N-dimethyl-2-(4-oxocyclohexyl)acetamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

NEt3 (2.0 ml) and TBTU (2.56 g) are added to a solution of 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetic acid (1.45 g; see J. Med. Chem. 1998, 41(5), 760) in DMF (50 ml) and the mixture is stirred for 30 min. 2 M Dimethylamine in THF (7.24 ml) is added. The reaction mixture is stirred for one hour and the solvent is removed under reduced pressure. The residue is dissolved in EtOAc and washed with water and aqueous citric acid (10%, 2×). The organic layer is dried (Na2SO4) and filtered, and the solvent is removed under reduced pressure. The crude product is purified using reverse phase HPLC (Varian C18 Microsorb) eluting with a gradient of 10-100% acetonitrile in water containing 0.2% trifluoroacetic acid to give N,N-dimethyl-2-(1,4-dioxaspiro[4.5]decan-8-yl)acetamide (400 mg) and N,N-dimethyl-2-(4-oxocyclohexyl)acetamide (420 mg).

後処理

  1. stirringThe reaction mixture is stirred for one hour
  2. customthe solvent is removed under reduced pressure
  3. dissolutionThe residue is dissolved in EtOAc
  4. washwashed with water and aqueous citric acid (10%, 2×)
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent is removed under reduced pressure
  8. customThe crude product is purified
  9. washeluting with a gradient of 10-100% acetonitrile in water containing 0.2% trifluoroacetic acid

出典と根拠

ORDレコード
ord-5f3c4ec7742b428bbae9689e0624cbbe
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08653262B2

反応ノート

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