Pyridine → HCID 86690247、化合物

HRID 80754ノート

反応式

HRID 80754 の反応式
[CH3:1][C@@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[CH3:15][C:16](OC(C)=O)=[O:17].N1C=CC=CC=1>C(Cl)Cl.CCOC(C)=O>[C:16]([N:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[C@H:2]([CH3:1])[CH2:7]1)(=[O:17])[CH3:15]

参加物

6

反応物 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 10262201tert-Butyl (2R)-2-methylpiperazine-1-carboxylate

生成物 1

HCID 86690247HCID 86690247、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of (R)-tert-butyl 2-methylpiperazine-1-carboxylate (4.8 g, 23.97 mmol), Ac2O (3.39 mL, 36.0 mmol) and pyridine (3.88 mL, 47.9 mmol) in DCM (30 mL) was stirred at rt for 30 min. Reaction was diluted with EtOAc, washed with diluted HCl, brine and sat NaHCO3, brine, and dried over Na2SO4, concentrated. Resulting residue was treated with 1N NaOH in ether, extracted with ether, washed with brine, dried over Na2SO4, concentrated and purified by FCC (0-10% MeOH in DCM) to give (R)-tert-butyl 4-acetyl-2-methylpiperazine-1-carboxylate. 1H NMR (400 MHz, CD2Cl2) δ ppm 4.14-4.46 (m, 2 H) 3.74-3.91 (m, 1 H) 3.46-3.72 (m, 1 H) 2.92-3.35 (m, 2 H) 2.56-2.91 (m, 1 H) 2.05 (d, J=16.67 Hz, 3 H) 1.44 (s, 9 H) 1.03-1.18 (m, 3 H). MS (ESI+) m/z 243.2 (M+H)+.

後処理

  1. customReaction
  2. washwashed with diluted HCl, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. additionResulting residue was treated with 1N NaOH in ether
  6. extractionextracted with ether
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated
  10. custompurified by FCC (0-10% MeOH in DCM)

出典と根拠

ORDレコード
ord-bc8910e6209f469f9b626f2ce285e8bc
出典データセット
uspto-grants-2014_09
特許番号
US08846656B2

反応ノート

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