Sodium Carbonate → tert-butyl 4-(4,5-dimethyl-2-propionylphenyl)-3,6-dihydropyridine-1(2H)-carboxylate

HRID 29724

反応式

HRID 29724 の反応式
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([CH3:14])=[CH:9][C:8]=1[C:15](=[O:18])[CH2:16][CH3:17])(=O)=O.C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:35]2[CH2:36][CH2:37][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:39][CH:40]=2)O1>C(O)C.C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][C:10]1[C:11]([CH3:13])=[CH:12][C:7]([C:35]2[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH:36]=2)=[C:8]([C:15](=[O:18])[CH2:16][CH3:17])[CH:9]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 586600794,5-Dimethyl-2-propionylphenyl trifluoromethanesulfonate

生成物 1

HCID 59788286tert-butyl 4-(4,5-dimethyl-2-propionylphenyl)-3,6-dihydropyridine-1(2H)-carboxylate

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 21863594Toluene ethanol溶媒

反応条件

温度
75 °C

実験手順

A vigorously stirred solution of triflate 83 (10.5 g, 33.8 mmol), aqueous sodium carbonate (50.8 mL of a 2.0 M solution, 102 mmol), tert-butyl 4(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)carboxylate (10.45 g, 33.8 mmol), and tetrakis(triphenylphosphine)palladium(0) (3.91 g, 3.38 mmol) in ethanol/toluene (1:1, 100 mL) was degassed via three vacuum/nitrogen ingress cycles and heated to 75° C. for 30 min. The reaction mixture was poured into ice water and extracted three times with EtOAc. The combined organic extracts were washed with brine, dried (MgSO4), filtered, and the filtrate concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-25% EtOAc/hexanes as eluent) afforded 84 as a colorless oil.

後処理

  1. extractionextracted three times with EtOAc
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 0%-25% EtOAc/hexanes as eluent)

出典と根拠

ORDレコード
ord-24a1e72a66c94072b2045f420f5e48c2
出典データセット
uspto-grants-2008_09
特許番号
US07419990B2

関連ノート

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