Imidazole → Tert-butyl 3-(iodomethyl)piperidine-1-carboxylate

HRID 602128노트

반응식

HRID 602128 반응식
N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:25]I.[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][CH2:37][CH:36]([CH2:40]O)[CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]>C1C=CC=CC=1>[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][CH2:37][CH:36]([CH2:40][I:25])[CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 2763851tert-Butyl 3-(hydroxymethyl)piperidine-1-carboxylate

생성물 1

HCID 20716152Tert-butyl 3-(iodomethyl)piperidine-1-carboxylate수율 96.3%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

Imidazole (1.58 g, 23.2 mmol), triphenylphosphine (6.09 g, 23.2 mmol) and iodine (4.72 g, 18.6 mmol) were added to 1-(tert-butoxycarbonyl)piperidin-3-yl methanol (2.00 g, 9.29 mmol) in benzene (50 mL). The mixture was stirred at room temperature for 3 hours. Subsequently, the reaction mixture was filtered through Celite and the solvent was evaporated. Water was added to the residue and the mixture was extracted with ethyl acetate. The extract was washed with brine and was dried over magnesium sulfate, followed by evaporation of the solvent. Purification of the residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1) gave 2.91 g (96%) of the desired compound as a pale yellow oil.

후처리

  1. filtrationSubsequently, the reaction mixture was filtered through Celite
  2. customthe solvent was evaporated
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialwas dried over magnesium sulfate
  7. customfollowed by evaporation of the solvent
  8. customPurification of the residue by silica gel column chromatography (hexane:ethyl acetate=20:1->5:1)

출처 및 근거

ORD 기록
ord-5b4128e737e94f5e9ffb97cc5e691afa
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902367B2

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