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

HRID 278232

反応式

HRID 278232 の反応式
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

参加物

10

反応物 5

HCID 795ImidazoleHCID 807Iodine2 回HCID 11776TriphenylphosphineHCID 24477Sodium ThiosulfateHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

生成物 1

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

試薬・触媒・溶媒 4

HCID 24462Copper Sulfate触媒HCID 3283Diethyl Ether溶媒2 回HCID 6342Acetonitrile溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c83c962e4a924518a69d95c326d2625c
出典データセット
uspto-grants-2002_03
特許番号
US06358979B1

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