Imidazole → Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate

HRID 278232

반응식

HRID 278232 반응식
O[CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:41]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(#N)C.CCOCC.[Cl-].[Na+].O.[O-]S([O-])(=O)=O.[Cu+2]>[I:41][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

참가 물질

10

반응물 5

HCID 795ImidazoleHCID 807Iodine2회HCID 11776TriphenylphosphineHCID 24477Sodium ThiosulfateHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

생성물 1

HCID 9974426Tert-butyl 4-(2-iodoethyl)piperidine-1-carboxylate

시약·촉매·용매 4

HCID 24462Copper Sulfate촉매HCID 3283Diethyl Ether용매2회HCID 6342Acetonitrile용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
0 °C

실험 절차

Combined 4-(2-hydroxyeth-1-yl)-1-tert-butoxylcarbonylpiperidine (37.4 g, 0.16 mol, from Step B), triphenylphosphine (55 g, 0.21 mol) and imidazole (14 g, 0.21 mol) in 800 mL of 33% acetonitrile in ether. Cooled to 0° C. and added iodine (56 g, 0.22 mol) portionwise. The iodine is de-colored until the endpoint of the reaction. Diluted with 1 L of ether. Washed organic layer with 2×500 mL each of sat'd. aq. Na2S2O3, sat. aq. CuSO4 and brine. Dried over magnesium sulfate, filtered and concentrated. Triphenylphosphine oxide precipitates. Added ether and filtered the slurry through a plug of silica gel. Purified a portion of the crude material by flash chromatography (5% ethyl acetate in hexane eluent) to afford the title compound.

후처리

  1. dry with materialDried over magnesium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customTriphenylphosphine oxide precipitates
  5. filtrationAdded ether and filtered the slurry through a plug of silica gel
  6. customPurified a portion of the crude material by flash chromatography (5% ethyl acetate in hexane eluent)

출처 및 근거

ORD 기록
ord-c83c962e4a924518a69d95c326d2625c
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06358979B1

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