Piperidine → HCID 54369926, 화합물

HRID 321947노트

반응식

HRID 321947 반응식
[Si:1]([N:8]1[C@@H:11]([CH2:12]I)[CH2:10][C:9]1=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>>[Si:1]([N:8]1[C@@H:11]([CH2:12][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH2:10][C:9]1=[O:14])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

3

반응물 2

HCID 8082PiperidineHCID 12944336HCID 12944336, 화합물

생성물 1

HCID 54369926HCID 54369926, 화합물수율 71%

실험 절차

1-(tert-butyldimethylsilyl)-4(R)-(iodomethyl)-azetidin-2-one (202 mg, 0.62 mmol) was heated at reflux in piperidine (5 mL) for 2 h. The solution was concentrated, dissolved in CH2Cl2 and washed with saturated NaHCO3 and brine, dried (MgSO4) and concentrated. The residue was purified by flash chromatography (SiO2, EtOAc) to give 1-(tert-butyldimethylsilyl)-4(R)-(piperidin-1-ylmethyl)azetidin-2-one (116 mg, 71% yield). 1H NMR (400 MHz, CDCl3) δ 3.70-3.63 (m, 1H), 3.16 (dd, J=15.3, 5.4 Hz, 1H), 2.70-2.61 (m, 2H), 2.45-2.26 (m, 5H), 1.60-1.53 (m, 4H), 1.46-1.38 (m, 2H), 0.96 (s, 9H), 0.24 (s, 6H).

후처리

  1. concentrationThe solution was concentrated
  2. dissolutiondissolved in CH2Cl2
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (SiO2, EtOAc)

출처 및 근거

ORD 기록
ord-2934af24513443bda3f6f90cf48c9283
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211170B1

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