Furan, 2-(bromomethyl)tetrahydro- → 1-(Ethylsulfonyl)-4-[(tetrahydro-2-furanyl)methyl]-4-piperidinecarbonitrile

HRID 551159노트

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HRID 551159 반응식
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][CH:9]([C:12]#[N:13])[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].Br[CH2:15][CH:16]1[CH2:20][CH2:19][CH2:18][O:17]1>C1(C)C=CC=CC=1>[CH2:1]([S:3]([N:6]1[CH2:7][CH2:8][C:9]([CH2:15][CH:16]2[CH2:20][CH2:19][CH2:18][O:17]2)([C:12]#[N:13])[CH2:10][CH2:11]1)(=[O:4])=[O:5])[CH3:2]

참가 물질

4

반응물 2

HCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 39240504HCID 39240504, 화합물

생성물 1

HCID 579311911-(Ethylsulfonyl)-4-[(tetrahydro-2-furanyl)methyl]-4-piperidinecarbonitrile

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

In a dry round bottom flask was placed 1-(ethylsulfonyl)-4-ethynylpiperidine (14) (6.7 g, 33.1 mmol) and anhydrous toluene (200 ml). To this was added 2-(bromomethyl)tetrahydrofuran (6.51 ml, 49.7 mmol). Solid KHMDS1.2 equiv (7.93 g, 39.7 mmol) was added in one portion at room temperature and an exotherm was observed. The solution was allowed to stir for 12 hours at which time it was quenched with saturated aq. NH4Cl solution (100 ml). To the mixture was added EtOAc (50 ml) and the solution was then extracted by dilution with 250 ml, water and 3 washes with EtOAc (75 ml each). The organic layer was washed with brine (200 ml) and dried over MgSO4. The organic solvent was removed in vacuo to give a yellow solid. The residue was purified by column chromatography on silica gel, eluting with EtOAc/Hexanes to give 1-(ethylsulfonyl)-4-(tetrahydrofuran-2-ylmethyl)piperidine-4-carbonitrile (15) as a off-white solid. MS 287 (M+1)

후처리

  1. customIn a dry round bottom flask was placed
  2. addition2 equiv (7.93 g, 39.7 mmol) was added in one portion at room temperature
  3. customwas quenched with saturated aq. NH4Cl solution (100 ml)
  4. additionTo the mixture was added EtOAc (50 ml)
  5. extractionthe solution was then extracted by dilution with 250 ml, water and 3
  6. washThe organic layer was washed with brine (200 ml)
  7. dry with materialdried over MgSO4
  8. customThe organic solvent was removed in vacuo
  9. customto give a yellow solid
  10. customThe residue was purified by column chromatography on silica gel
  11. washeluting with EtOAc/Hexanes

출처 및 근거

ORD 기록
ord-3f791c5bc65d4f0393395454e7b5ded5
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947714B2

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