Piperidine → HCID 54369926、化合物

HRID 321947ノート

反応式

HRID 321947 の反応式
[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]

参加物

3

反応物 2

HCID 8082PiperidineHCID 12944336HCID 12944336、化合物

生成物 1

HCID 54369926HCID 54369926、化合物収率 71%

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2934af24513443bda3f6f90cf48c9283
出典データセット
uspto-grants-2001_04
特許番号
US06211170B1

反応ノート

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