Diisopropylethylamine → tert-Butyl 4-(4-methanesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)piperazine-1-carboxylate

HRID 1295559ノート

反応式

HRID 1295559 の反応式
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][CH2:9][N:8]([S:12]([CH3:15])(=[O:14])=[O:13])[C:7]=2[CH:16]=1.[N:17]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N(CC)C(C)C)(C)C>CC(O)C>[CH3:15][S:12]([N:8]1[C:7]2[CH:16]=[C:3]([CH2:2][N:20]3[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21]3)[CH:4]=[CH:5][C:6]=2[O:11][CH2:10][CH2:9]1)(=[O:14])=[O:13]

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 694200776-Bromomethyl-4-methanesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazine

生成物 1

HCID 86597571tert-Butyl 4-(4-methanesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)piperazine-1-carboxylate収率 71.5%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

6-Bromomethyl-4-methanesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazine (2.6 g, 8.5 mmol) and tert-butyl piperazine-1-carboxylate (1.58 g, 8.5 mmol) were treated with propan-2-ol (100 mL) followed by N,N-diisopropylethylamine (10.96 g, 85 mmol) and the resulting mixture heated at reflux for 72 h then evaporated to dryness under reduced pressure. The residue was partitioned between ethyl acetate and saturated NaHCO3 aq. and the phases separated. The organic phase was washed with water, saturated brine, dried (MgSO4) and evaporated to dryness under reduced pressure. Chromatography on SiO2, eluting with ethyl acetate in 60°–80° petroleum ether, gave the title compound (2.5 g, 71%) as a brown foam.

後処理

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 72 h
  3. customthen evaporated to dryness under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and saturated NaHCO3 aq.
  5. customthe phases separated
  6. washThe organic phase was washed with water, saturated brine
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness under reduced pressure
  9. washChromatography on SiO2, eluting with ethyl acetate in 60°–80° petroleum ether

出典と根拠

ORDレコード
ord-2859919803cd427ea887c1b1fcc014f3
出典データセット
uspto-grants-2007_07
特許番号
US07244726B2

反応ノート

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