Imidazole → tert-butyl-4-[(1R,2R)-2-(iodomethyl)cyclopropyl]piperidine-1-carboxylate

HRID 1468823노트

반응식

HRID 1468823 반응식
O[CH2:2][C@@H:3]1[CH2:5][C@@H:4]1[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:43]I>C1COCC1>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][CH:6]([C@H:4]2[CH2:5][C@H:3]2[CH2:2][I:43])[CH2:7][CH2:8]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 53393314HCID 53393314, 화합물

생성물 1

HCID 86717780tert-butyl-4-[(1R,2R)-2-(iodomethyl)cyclopropyl]piperidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Intermediate 4 (2.0 g, 7.8 mmol), PPh3 (2.68 g, 10.2 mmol), imidazole (1.07 g, 15.7 mmol), and iodine (2.98 g, 11.7 mmol) were dissolved in THF (15 mL), and the resulting solution was stirred at RT for 2 h. The solution was quenched with sat. Na2S2O3, and extracted with Et2O. The organic layer was dried over Na2SO4, filtered, and concentrated. The residue was purified by silica gel column chromatography (10/1 hexanes/EtOAc) which provided the title compound.

후처리

  1. customThe solution was quenched with sat. Na2S2O3
  2. extractionextracted with Et2O
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (10/1 hexanes/EtOAc) which

출처 및 근거

ORD 기록
ord-f50b51ae79fe44209a2b7e8ea6d90f59
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006228B2

반응 노트

불러오는 중…