Sodium Thiosulfate → 3-[5-Methanesulfonyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-propionaldehyde

HRID 271764

反応式

HRID 271764 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][S:24]([N:27]1[CH2:32][CH2:31][C:30]2[N:33]([CH2:46][CH2:47][CH2:48][OH:49])[N:34]=[C:35]([C:36]3[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=3)[C:29]=2[CH2:28]1)(=[O:26])=[O:25].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl.CCOCC.C([O-])(O)=O.[Na+]>[CH3:23][S:24]([N:27]1[CH2:32][CH2:31][C:30]2[N:33]([CH2:46][CH2:47][CH:48]=[O:49])[N:34]=[C:35]([C:36]3[CH:37]=[CH:38][C:39]([C:42]([F:43])([F:44])[F:45])=[CH:40][CH:41]=3)[C:29]=2[CH2:28]1)(=[O:26])=[O:25]

参加物

7

反応物 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 222936223-[5-Methanesulfonyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-propan-1-ol

生成物 1

HCID 222938973-[5-Methanesulfonyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-propionaldehyde収率 85.2%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

Dess-Martin periodinane (3.45 9, 8.2 mmol) was added to a solution of 3-[5-methanesulfonyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-propan-1-ol (3.0 g, 7.4 mmol) in CH2Cl2 (20 mL) at 0° C. under N2. After 15 min, the reaction was allowed to warm to room temperature and stirred for another 1.5 h. The reaction was diluted with Et2O (60 mL) and 20% aq. NaHCO3 (35 mL) was added slowly. Then Na2S2O3 was added and stirred at room temperature for 30 min. The layers were separated and the aqueous portion was extracted with Et2O (2×30 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. MPLC (1-10% MeOH/CH2Cl2) afforded 2.53 g of the desired aldehyde in 85% yield. MS (electrospray): calculated for C17H18F3N3O3S, 401.11; m/z found, 402.1 [M+H], 434.1 [M+MeOH+H]. 1H NMR (400 MHz, CDCl3): 9.82 (s, 1H), 7.63 (d, J=8.4 Hz, 2H), 7.58 (d, J=8.4 Hz, 2H), 4.68 (s, 2H), 4.25 (t, J=6.1 Hz, 2H), 3.63 (t, J=5.8 Hz, 4H), 3.14 (t, J=6.1 Hz, 2H), 2.92 (t, J=5.8 Hz, 2H), 2.81 (s, 3H).

後処理

  1. additionwas added slowly
  2. stirringstirred at room temperature for 30 min
  3. customThe layers were separated
  4. extractionthe aqueous portion was extracted with Et2O (2×30 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-53738a0cc0b24ae38253475140e96a3d
出典データセット
uspto-grants-2008_11
特許番号
US07452890B2

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