Tetrahydrofuran → HCID 69430054、化合物

HRID 1352670ノート

反応式

HRID 1352670 の反応式
[CH2:1]([Li])[CH2:2][CH2:3]C.[CH:6]([C@H:8]1[CH2:24][N:12]2[CH2:13][CH2:14][N:15]([C:17]3[N:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=3)[CH2:16][C@@H:11]2[CH2:10][CH2:9]1)=O.[CH2:25]1[CH2:29]O[CH2:27][CH2:26]1>[Cl-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1>[C:25]1([CH:29]=[CH:6][CH:8]2[CH2:24][N:12]3[CH2:13][CH2:14][N:15]([C:17]4[N:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]=4)[CH2:16][CH:11]3[CH2:10][CH2:9]2)[CH:3]=[CH:2][CH:1]=[CH:27][CH:26]=1

参加物

5

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 57161266HCID 57161266、化合物HCID 178418339Butyllithium

生成物 1

HCID 69430054HCID 69430054、化合物

試薬・触媒・溶媒 1

HCID 70671Benzyltriphenylphosphonium chloride触媒

実験手順

A solution of 1.70 g (4.38 mmol) of benzyl triphenyl phosphonium chloride in 20 mL of dry THF was chilled to −78° C. and treated with 1.75 mL (4.38 mmol) of n-butyllithium (2.5 M in hexane). After 15 min, 1.05 g (3.98 mmol) of (7R,9aS)-7-formyl-2-(5-fluoropyrimidin-2-yl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine in 20 mL of dry THF was added dropwise over 30 min, the cooling bath was removed and the solution allowed to warm slowly to ambient temperature overnight (16 h). The solution was concentrated in vacuo and the residue was partitioned between ethyl ether and water. The organic layer was dried (magnesium sulfate), filtered and evaporated. Purification by flash silica gel chromatography with petroleum ether:ethyl ether in ratios from 4:1 to 3:1 gave the following isomers of 7-(2-phenyl)ethenyl-2-(5-fluoropyrimidin-2-yl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine: E-(7S,9aS), 0.19 g (Rf=0.75 with 3:1 hexane:ethyl acetate); Z-(7R,9aS), 0.16 g (Rf=0.47 with 3:1 hexane:ethyl acetate); E-(7R,9aS), 0.46 g (Rf=23 with 3:1 hexane:ethyl acetate).

後処理

  1. customthe cooling bath was removed
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was partitioned between ethyl ether and water
  4. dry with materialThe organic layer was dried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by flash silica gel chromatography with petroleum ether

出典と根拠

ORDレコード
ord-5c8bd2e5243043e0930211fb22ae1398
出典データセット
uspto-grants-2007_05
特許番号
US07220753B2

反応ノート

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