Imidazole → Tert-butyl 4-iodopiperidine-1-carboxylate

HRID 1019000

反応式

HRID 1019000 の反応式
[I:1]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.O[CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]1>C(#N)C.C(OCC)C>[I:1][CH:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]1

参加物

7

反応物 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

生成物 1

HCID 10892302Tert-butyl 4-iodopiperidine-1-carboxylate

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒2 回

実験手順

86 g of iodine are added at ambient temperature to a suspension of 89 g of triphenylphosphine and 22 g of imidazole in 800 ml of acetonitrile. The reaction is exothermic. After return to ambient temperature, 45.9 g of the product obtained in Step 1 in 250 ml of acetonitrile are added in the course of 30 minutes. After 18 hours' stirring at ambient temperature, the reaction mixture is filtered and rinsed with 200 ml of acetonitrile and the resulting filtrate is concentrated in vacuo. The residue obtained is stirred in 250 ml of diethyl ether for 1 hour and the precipitate is filtered off. After concentration of the filtrate in vacuo, chromatography on silica gel (dichloromethane/ethyl acetate: 90/10) enables the expected product to be isolated.

後処理

  1. filtrationthe reaction mixture is filtered
  2. washrinsed with 200 ml of acetonitrile
  3. concentrationthe resulting filtrate is concentrated in vacuo
  4. customThe residue obtained
  5. filtrationthe precipitate is filtered off
  6. customto be isolated

出典と根拠

ORDレコード
ord-bf2d29da904a4c639c0b64cfd009a431
出典データセット
uspto-grants-2002_11
特許番号
US06486171B2

関連ノート

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