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Triacetoxyperiodinane → (S)-Ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-formyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

HRID 921102
ノート
印刷プレビュー

反応式

HRID 921102 の反応式
[CH2:1]([O:4][C:5]1([CH3:34])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([CH2:20][OH:21])[CH:19]=[C:15]3[N:14]=[C:13]([CH3:22])[C:12]=2[C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:7][CH2:6]1)[CH:2]=[CH2:3].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH2:1]([O:4][C:5]1([CH3:34])[CH2:10][CH2:9][N:8]([C:11]2[N:16]3[N:17]=[C:18]([CH:20]=[O:21])[CH:19]=[C:15]3[N:14]=[C:13]([CH3:22])[C:12]=2[C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:7][CH2:6]1)[CH:2]=[CH2:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 118318735(S)-Ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(hydroxymethyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate

生成物 1

HCID 118318786(S)-Ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-formyl-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate収率 71.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (S)-ethyl 2-(7-(4-(allyloxy)-4-methylpiperidin-1-yl)-2-(hydroxymethyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl)-2-(tert-butoxy)acetate (0.2747 g, 0.579 mmol) in wet DCM (5 mL) was added Dess-Martin periodinane (0.319 g, 0.752 mmol) and the mixture was stirred at room temperature. After 3 h, the solids were removed by filtration. The filtrate was washed with aq Na2S2O3, dried (Na2SO4), filtered and concentrated. The resulting oil was purified by flash chromatography (Biotage; 0%-50% EtOAc/hexane; 10 CV) to give the title compound (0.1962 g, 0.415 mmol, 71.7% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 10.17 (s, 1H), 7.02 (s, 1H), 6.19-5.98 (m, 1H), 5.96-5.76 (m, 1H), 5.57-5.37 (m, 2H), 5.24 (dd, J=10.4, 1.6 Hz, 1H), 4.24 (dd, J=15.9, 7.1 Hz, 2H), 4.03 (d, J=4.9 Hz, 2H), 2.65 (s, 3H), 2.08-1.93 (m, 5H), 1.81-1.66 (m, 1H), 1.37 (s, 3H), 1.29-1.25 (m, 12H). 2 piperidine protons not seen by NMR. LCMS (M+H) calcd for C25H37N4O5: 473.27. found: 473.3.

後処理

  1. customthe solids were removed by filtration
  2. washThe filtrate was washed with aq Na2S2O3
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting oil was purified by flash chromatography (Biotage; 0%-50% EtOAc/hexane; 10 CV)

出典と根拠

ORDレコード
ord-0825a6ab5f024857b09737c36297f6e9
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09273067B2

反応ノート

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