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

HRID 1468823ノート

反応式

HRID 1468823 の反応式
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]

参加物

6

反応物 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 53393314HCID 53393314、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f50b51ae79fe44209a2b7e8ea6d90f59
出典データセット
uspto-grants-2015_04
特許番号
US09006228B2

反応ノート

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