Triphenylphosphine → 2,2-dimethyl-N-[6-(4-trifluoromethyl-phenoxymethyl)-pyridin-2-yl]-propionamide

HRID 1454827ノート

反応式

HRID 1454827 の反応式
[OH:1][CH2:2][C:3]1[N:8]=[C:7]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:35][C:36]([F:45])([F:44])[C:37]1[CH:42]=[CH:41][C:40](O)=[CH:39][CH:38]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[CH3:13][C:11]([CH3:12])([CH3:14])[C:10]([NH:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][O:1][C:40]2[CH:41]=[CH:42][C:37]([C:36]([F:45])([F:44])[F:35])=[CH:38][CH:39]=2)[N:8]=1)=[O:15]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 678744-(Trifluoromethyl)phenolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 21782926N-[6-(Hydroxymethyl)pyridin-2-yl]-2,2-dimethylpropanamide

生成物 1

HCID 688432242,2-dimethyl-N-[6-(4-trifluoromethyl-phenoxymethyl)-pyridin-2-yl]-propionamide収率 92.8%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

N-(6-Hydroxymethyl-pyridin-2-yl)-2,2-dimethyl-propionamide (0.625 g), triphenylphophine (0.786 g) and 4-trifluoromethyl-phenol (0.486 g) in toluene was treated at RT under an argon atmosphere with diisopropyl azodicarboxylate (0.67 g). The mixture was stirred for 2 h, partitioned between ice water and AcOEt, the layers were separated, the aqueous layer twice extracted with AcOEt. The combined organic layers were washed with water and saturated aqueous NaCl, dried over MgSO4, filtered and evaporated. The residue was purified by flash chromatography (heptane/AcOEt 100 to 85%) to give 2,2-dimethyl-N-[6-(4-trifluoromethyl-phenoxymethyl)-pyridin-2-yl]-propionamide (0.98 g) as a yellow oil. MS (ESI): 353.2 (MH+).

後処理

  1. custompartitioned between ice water and AcOEt
  2. customthe layers were separated
  3. extractionthe aqueous layer twice extracted with AcOEt
  4. washThe combined organic layers were washed with water and saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by flash chromatography (heptane/AcOEt 100 to 85%)

出典と根拠

ORDレコード
ord-95b6212040154c8ea5f1448012f0e1a4
出典データセット
uspto-grants-2009_01
特許番号
US07482341B2

反応ノート

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