Potassium Iodide → 4-{4-[(1-isopropylazetidin-3-yl)methoxy]phenyl}tetrahydro-2H-pyran-4-carbonitrile

HRID 273078ノート

反応式

HRID 273078 の反応式
Cl.Cl[CH2:3][CH:4]1[CH2:7][N:6]([CH:8]([CH3:10])[CH3:9])[CH2:5]1.[OH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2([C:24]#[N:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C=O)C>[CH:8]([N:6]1[CH2:7][CH:4]([CH2:3][O:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3([C:24]#[N:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[CH:14][CH:13]=2)[CH2:5]1)([CH3:10])[CH3:9]

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 230916094-(4-Hydroxy-phenyl)-tetrahydro-pyran-4-carbonitrileHCID 685790653-(Chloromethyl)-1-isopropylazetidine hydrochloride

生成物 1

HCID 598374014-{4-[(1-isopropylazetidin-3-yl)methoxy]phenyl}tetrahydro-2H-pyran-4-carbonitrile収率 60.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-(chloromethyl)-1-isopropylazetidine hydrochloride (2.8 g, 15.2 mmol), 4-(4-hydroxyphenyl)tetrahydropyran-4-carbonitrile (3.1 g, 15.2 mmol) and potassium carbonate (8.5 g, 61.6 mmol) were combined in DMF (40 ml) and stirred at 500 for 2 hours. Potassium iodide (0.5 g 3.0 mmol) was added and the mixture was stirred at 50° for 18 hours then at 90-95° for a further 5 hours. The reaction mixture was concentrated in vacuo then partitioned between ethyl acetate (80 ml) and water (50 ml). The ethyl acetate was washed with saturated NaCl (50 ml) then dried over Na2SO4 and concentrated in vacuo to give a brown semi-crystalline material which was triturated with diisopropyl ether (25 ml) to give the title compound as a beige powder (2.9 g, 60%). 1H NMR (400 MHz, CDCl3) δ7.38 (d, 2H), 6.91 (d, 2H), 4.08 (m, 4H), 3.89 (m, 2H), 3.41 (t, 2H), 3.02 (t, 2H), 2.87 (m, 1H), 2.31 (m, 1H), 2.15-2.00 (m, 4H), 0.94 (d, 6H).

後処理

  1. stirringthe mixture was stirred at 50° for 18 hours
  2. waitat 90-95° for a further 5 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthen partitioned between ethyl acetate (80 ml) and water (50 ml)
  5. washThe ethyl acetate was washed with saturated NaCl (50 ml)
  6. dry with materialthen dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto give a brown semi-crystalline material which
  9. customwas triturated with diisopropyl ether (25 ml)

出典と根拠

ORDレコード
ord-5f8a5fee1a294e6689badaa9c69fa8ab
出典データセット
uspto-grants-2008_11
特許番号
US07456164B2

反応ノート

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