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

HRID 1019000노트

반응식

HRID 1019000 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bf2d29da904a4c639c0b64cfd009a431
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06486171B2

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