Tetrahydro-4H-pyran-4-one → HCID 11650188、化合物

HRID 2099353ノート

反応式

HRID 2099353 の反応式
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([CH2:6][C@H:7]([C:9]([N:11]2[CH:16]3[CH2:17][CH2:18][CH:12]2[CH2:13][CH:14]([N:19]([CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:20]([N:22]([CH2:25][CH3:26])[CH2:23][CH3:24])=[O:21])[CH2:15]3)=[O:10])[NH2:8])=[CH:4][CH:3]=1.[O:35]1[CH2:40][CH2:39][C:38](=O)[CH2:37][CH2:36]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@H:7]([C:9]([N:11]2[CH:16]3[CH2:17][CH2:18][CH:12]2[CH2:13][CH:14]([N:19]([CH:27]2[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)[C:20]([N:22]([CH2:23][CH3:24])[CH2:25][CH3:26])=[O:21])[CH2:15]3)=[O:10])[NH:8][CH:38]2[CH2:39][CH2:40][O:35][CH2:36][CH2:37]2)=[CH:33][CH:34]=1

参加物

5

反応物 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 68829063HCID 68829063、化合物

生成物 1

HCID 11650188HCID 11650188、化合物収率 65.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

0.30 g of the N-[8-(4-chloro-D-phenylalanyl)-8-azabicyclo[3.2.1]oct-3-yl]-N-cyclohexyl-N′,N′-diethylurea endo compound, obtained in step 1.5, is dissolved in 3 ml of dichloromethane under N2 in the presence of 0.061 g of tetrahydro-4H-pyran-4-one and of 0.17 g of sodium triacetoxyborohydride. The reaction medium is stirred at ambient temperature for 3 days. After evaporation and hydrolysis with a saturated aqueous sodium hydrogen carbonate solution, extraction is carried out with ethyl acetate until the aqueous phase is completely depleted. The organic phase is washed with H2O and then with a saturated aqueous sodium chloride solution. Drying over MgSO4 and concentration to dryness are carried out. The crude is chromatographed on silica gel, elution being carried out with a 99/1 and then 98/2 mixture of dichloromethane and methanol. 0.23 g of N-{8-[4-chloro-N-(tetrahydro-2H-pyran-4-yl)-D-phenylalanyl]-8-azabicyclo[3.2.1]oct-3-yl}-N-cyclohexyl-N′,N′-diethylurea is then obtained.

後処理

  1. customobtained in step 1.5
  2. customAfter evaporation and hydrolysis
  3. extractionwith a saturated aqueous sodium hydrogen carbonate solution, extraction
  4. washThe organic phase is washed with H2O
  5. dry with materialDrying over MgSO4 and concentration to dryness
  6. customThe crude is chromatographed on silica gel, elution
  7. addition98/2 mixture of dichloromethane and methanol

出典と根拠

ORDレコード
ord-a8adbb1096fa4d39909fe2338203a82b
出典データセット
uspto-grants-2009_08
特許番号
US07569582B2

反応ノート

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