Potassium Carbonate → 2'-(Benzyloxy)-2-[4-(tert-butoxycarbonyl)piperazin-1-yl]-4'-fluoroacetophenone

HRID 1433150

反応式

HRID 1433150 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14]([O:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[C:29](=[O:32])[CH2:30]Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:14]([O:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[C:29](=[O:32])[CH2:30][N:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 579348132'-(Benzyloxy)2-bromo4'-fluoroacetophenone

生成物 1

HCID 690593352'-(Benzyloxy)-2-[4-(tert-butoxycarbonyl)piperazin-1-yl]-4'-fluoroacetophenone収率 80.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1-(tert-Butoxycarbonyl)piperazine (808 mg, 4.34 mmol) was added to a mixture of 2′-(benzyloxy)-2-bromo4′-fluoroacetophenone (assumed 4.13 mmol) and potassium carbonate (856 mg, 6.20 mmol) in DMF, and stirred for 18 h at room temperature. The solvent was removed in vacuo, the residue taken up in ethyl acetate (150 mL) and washed with water (100 mL) and brine (100 mL). The organice layer was dried (MgSO4) and the solvents removed in vacuo. The crude product was purified by flash chromatography, eluting with 9:1 hexane:EtOAc followed by 1:1 hexane:EtOAc to give pure 2′-(benzyloxy)-2-[4-(tert-butoxycarbonyl)piperazin-1-yl]-4′-fluoroacetophenone (1.42 g, 80% over 2 steps) as a yellow oil; Rf 0.00 (9:1 hexane:EtOAc), 0.50 (1:1 hexane:EtOAc); δH (CDCl3) 7.89 (1H, dd, J=9.3 and 6.9 Hz), 7.48-7.44 (5H, m), 6.81-6.77 (2H, m), 5.17 (2H, s), 3.79 (2H, s), 3.51-3.47 (4H, m), 2.44-2.41 (4H, m), 1.50 (9H, s); LCMS retention time 2.10 min, M+H+ 429.4.

後処理

  1. customThe solvent was removed in vacuo
  2. washwashed with water (100 mL) and brine (100 mL)
  3. dry with materialThe organice layer was dried (MgSO4)
  4. customthe solvents removed in vacuo
  5. customThe crude product was purified by flash chromatography
  6. washeluting with 9:1 hexane

出典と根拠

ORDレコード
ord-f03db8d5639144f7af01926186f81cb1
出典データセット
uspto-grants-2009_11
特許番号
US07612201B2

関連ノート

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