Benzyl chloroformate → benzyl 4-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine-1-carboxylate

HRID 517559ノート

反応式

HRID 517559 の反応式
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)[CH:10]=1.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>CO.[OH-].[Na+]>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([N:15]2[CH2:20][CH2:19][N:18]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[CH2:17][CH2:16]2)[CH:10]=1

参加物

5

反応物 2

HCID 10387Benzyl chloroformateHCID 867114981-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine

生成物 1

HCID 86711499benzyl 4-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine-1-carboxylate収率 58%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

To a solution of 1-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine (8.5 g, 30.6 mmol) in MeOH (30 mL), NaOH (2 M, 31 mL) was slowly added at RT, followed by the addition of benzyl chloroformate (6.4 g, 37 mmol) in portions at 0° C. The mixture was stirred at RT overnight. The solution was concentrated and diluted with H2O (500 mL), extracted with EtOAc (3×200 mL). The combined organic layers were washed with H2O (100 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated to afford the crude product, which was purified by silica gel column chromatography (Petroleum ether:EtOAc=1:1) to afford benzyl 4-(4-((tetrahydro-2H-pyran-2-yloxy)methyl)pyridin-2-yl)piperazine-1-carboxylate as a yellow oil (7.3 g, 58%). MS (ES+) C23H29N3O4 requires: 411, found: 412[M+H]+.

後処理

  1. concentrationThe solution was concentrated
  2. additiondiluted with H2O (500 mL)
  3. extractionextracted with EtOAc (3×200 mL)
  4. washThe combined organic layers were washed with H2O (100 mL) and brine (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford the crude product, which
  9. customwas purified by silica gel column chromatography (Petroleum ether:EtOAc=1:1)

出典と根拠

ORDレコード
ord-700a54ea03bc4284ade81f11679fbda5
出典データセット
uspto-grants-2015_08
特許番号
US09115120B2

反応ノート

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