Tetrahydrofuran → HCID 69430054, 화합물

HRID 1977017노트

반응식

HRID 1977017 반응식
[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

참가 물질

5

반응물 3

HCID 8028Tetrahydrofuran2회HCID 57161266HCID 57161266, 화합물HCID 178418339Butyllithium

생성물 1

HCID 69430054HCID 69430054, 화합물

시약·촉매·용매 1

HCID 70671Benzyltriphenylphosphonium chloride촉매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-16fd50ce3a08404a8318e415b4397d58
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06231833B1

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