(Dimethyl sulfide)trihydroboron → n[3,5-Bis(3-methoxypropyl)benzyl]cyclopropanamine

HRID 658252ノート

反応式

HRID 658252 の反応式
[CH:1]1([NH:4][C:5](=O)[C:6]2[CH:11]=[C:10]([CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:9]=[C:8]([CH2:17][CH2:18][CH2:19][O:20][CH3:21])[CH:7]=2)[CH2:3][CH2:2]1.B.CSC>C1COCC1>[CH3:21][O:20][CH2:19][CH2:18][CH2:17][C:8]1[CH:7]=[C:6]([CH:11]=[C:10]([CH2:12][CH2:13][CH2:14][O:15][CH3:16])[CH:9]=1)[CH2:5][NH:4][CH:1]1[CH2:2][CH2:3]1

参加物

4

反応物 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 57456873N-cyclopropyl-3,5-bis(3-methoxypropyl)benzamide

生成物 1

HCID 59234217n[3,5-Bis(3-methoxypropyl)benzyl]cyclopropanamine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-cyclopropyl-3,5-bis(3-methoxypropyl)benzamide (1 eq.) from the previous step in THF (0.18 M) at 80° C. was added borane-dimethylsulfide (10 eq.). The reaction was distilled to about half volume and heated under reflux for 3 h. Then, the reaction was cooled to rt and slowly quenched with 10% HCl aqueous solution. The reaction was heated to reflex again and stirred for 45 min. After cooling to rt, the reaction was diluted with EtOAc and basified with aqueous NaOH solution (pH >10). The organic extract was washed with saturated aqueous NaHCO3, brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 25% EtOAc in Hex plus 3% Et3N) to afford the title compound amine 3 as an oil.

後処理

  1. distillationThe reaction was distilled to about half volume
  2. temperatureheated
  3. temperatureunder reflux for 3 h
  4. customslowly quenched with 10% HCl aqueous solution
  5. temperatureThe reaction was heated
  6. temperatureAfter cooling to rt
  7. additionthe reaction was diluted with EtOAc and basified with aqueous NaOH solution (pH >10)
  8. extractionThe organic extract
  9. washwas washed with saturated aqueous NaHCO3, brine
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated in vacuo
  12. customThe crude product was purified by flash column chromatography (SiO2, 25% EtOAc in Hex plus 3% Et3N)

出典と根拠

ORDレコード
ord-29c1838bf1864f0a83898f69620263d3
出典データセット
uspto-grants-2011_12
特許番号
US08076359B2

反応ノート

読み込み中…