Pyridine → HCID 86690247, 화합물

HRID 80754노트

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HRID 80754 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 86690247HCID 86690247, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-bc8910e6209f469f9b626f2ce285e8bc
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846656B2

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