Diethyl Ether → (1-Butyl-4-piperidinyl)methyl 3,4-dihydro-2H-pyrano[2,3-b]indolizine-10-carboxylate

HRID 1939254

반응식

HRID 1939254 반응식
[CH2:1]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][OH:12])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].C[Li].CCOCC.[O:20]1[C:25]2[C:26]([C:33](OCC)=[O:34])=[C:27]3[N:32]([C:24]=2[CH2:23][CH2:22][CH2:21]1)[CH:31]=[CH:30][CH:29]=[CH:28]3>C1COCC1>[O:20]1[C:25]2[C:26]([C:33]([O:12][CH2:11][CH:8]3[CH2:9][CH2:10][N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:6][CH2:7]3)=[O:34])=[C:27]3[N:32]([C:24]=2[CH2:23][CH2:22][CH2:21]1)[CH:31]=[CH:30][CH:29]=[CH:28]3

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 10241250(1-Butylpiperidin-4-yl)methanolHCID 21467249ethyl 3,4-dihydro-2H-pyrano[2,3-b]indolizine-10-carboxylateHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 21467257(1-Butyl-4-piperidinyl)methyl 3,4-dihydro-2H-pyrano[2,3-b]indolizine-10-carboxylate수율 79.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A stirred solution of (1-butyl-4-piperidinyl)methanol (125 mg, 0.72 mmole) in dry THF (5 ml) at 5° C. under argon was treated with 1.5M methyllithium in ether (0.35 ml, 0.50 mmole). After 10 minutes, a solution of ethyl 3,4-dihydro-2H-pyrano[2,3-b]indolizine-10-carboxylate (55 mg, 0.22 mmole) in dry THF (5 ml) was added and the mixture heated under reflux for 3 h. The mixture was then allowed to cool and concentrated in vacuo. The residue was treated with 10% Na2CO3 solution (10 ml) and extracted with ethyl acetate (2×40 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo to leave a yellow oil, which was chromatographed on silica gel eluting with 3% methanol/chloroform to afford the title compound as a pale pink oil (65 mg, 78%).

후처리

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 3 h
  3. temperatureto cool
  4. concentrationconcentrated in vacuo
  5. additionThe residue was treated with 10% Na2CO3 solution (10 ml)
  6. extractionextracted with ethyl acetate (2×40 ml)
  7. dry with materialThe combined extracts were dried (Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customto leave a yellow oil, which
  10. customwas chromatographed on silica gel eluting with 3% methanol/chloroform

출처 및 근거

ORD 기록
ord-1e67b804d765476a9bae59c2f9714b15
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05696129

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