Sodium hydride → Dibenz(b,E)(1,4)oxazepine, 5,11-dihydro-5-(((2R)-1-(2-(4-methoxyphenyl)ethyl)-2-pyrrolidinyl)methyl)-

HRID 365313ノート

反応式

HRID 365313 の反応式
[H-].[Na+].[CH:3]1[C:13]2[CH2:12][O:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[NH:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.Cl[C@H:19]1[CH2:24][CH2:23][CH2:22][N:21]([CH2:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[CH2:20]1>CS(C)=O>[CH3:34][O:33][C:30]1[CH:29]=[CH:28][C:27]([CH2:26][CH2:25][N:21]2[CH2:22][CH2:23][CH2:24][C@@H:20]2[CH2:19][N:8]2[C:7]3[CH:6]=[CH:5][CH:4]=[CH:3][C:13]=3[CH2:12][O:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]2=3)=[CH:32][CH:31]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 110847985,11-Dihydrodibenzo[b,e][1,4]oxazepineHCID 15481942(s)-(+)-3-Chloro-1-(4-methoxyphenethyl)piperidine

生成物 1

HCID 9823094Dibenz(b,E)(1,4)oxazepine, 5,11-dihydro-5-(((2R)-1-(2-(4-methoxyphenyl)ethyl)-2-pyrrolidinyl)methyl)-収率 70%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

Sixty-percent sodium hydride (520 mg, 13 mmols) was washed with petroleum ether, and then suspended in 55 ml of dimethyl sulfoxide. To the suspension were added 2.0 g (10 mmols) of 5,11-dihydrodibenzo[b,e][1,4]oxazepine. The mixture was stirred in a nitrogen atmosphere at room temperature for 40 minutes. To this reaction solution was added dropwise a solution of 3.1 g (12 mmols) of (S)-(+)-3-chloro-1-(4-methoxyphenethyl)piperidine [[α]D25 =+10.1° (c=1.2, ethanol)] in 10 ml of dimethyl sulfoxide, and the mixed solution was stirred at room temperature for 14 hours and at 40° C. for 6 hours. The reaction solution was poured into ice water, and extracted with ethyl acetate. The organic layer was washed with water and with a saturated aqueous solution of sodium chloride in this order, and dried. Subsequently, the solvent was distilled off under reduced pressure. The resulting residue was subjected to column chromatography, and eluted with a mixed solvent of ethyl acetate and hexane at a ratio of 1:2. This mixed solvent was distilled off under reduced pressure to give 2.9 g of (R)-(+)-5,11-dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]oxazepine as a pale yellow oil in a yield of 70%.

後処理

  1. stirringthe mixed solution was stirred at room temperature for 14 hours and at 40° C. for 6 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and with a saturated aqueous solution of sodium chloride in this order
  4. customdried
  5. distillationSubsequently, the solvent was distilled off under reduced pressure
  6. washeluted with a mixed solvent of ethyl acetate and hexane at a ratio of 1:2
  7. distillationThis mixed solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-dc363a2c2ac144fe90c4972083429cf8
出典データセット
uspto-grants-2000_10
特許番号
US06127361

反応ノート

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