Hydrochloric Acid → (R)-8-Bromo-3-(N-isopropylamino)-5-methoxy-3,4-dihydro-2H-1-benzopyran

HRID 52261

反応式

HRID 52261 の反応式
[CH:1]([NH:4][C@@H:5]1[CH2:10][C:9]2[C:11]([O:15][CH3:16])=[CH:12][CH:13]=[CH:14][C:8]=2[O:7][CH2:6]1)([CH3:3])[CH3:2].C([O-])(=O)C.[Na+].[Br:22]Br.Cl>C(O)(=O)C.C(OCC)C>[Br:22][C:14]1[C:8]2[O:7][CH2:6][C@H:5]([NH:4][CH:1]([CH3:3])[CH3:2])[CH2:10][C:9]=2[C:11]([O:15][CH3:16])=[CH:12][CH:13]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24408BromineHCID 517045Sodium AcetateHCID 10489181(R)-3-(N-Isopropylamino)-5-methoxychroman

生成物 1

HCID 54029305(R)-8-Bromo-3-(N-isopropylamino)-5-methoxy-3,4-dihydro-2H-1-benzopyran収率 62%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 3283Diethyl Ether溶媒

実験手順

(R)-3-(N-Isopropylamino)-5-methoxy-3,4-dihydro-2H-1-benzopyran (4.02 g, 18.2 mmol) and anhydrous sodium acetate were dissolved in acetic acid (80 mL). To the stirred mixture was bromine (0.93 mL, 18.2 mmol) dissolved in acetic acid (40 mL) added dropwise under 1.5 h. The solvent was removed in vacuo, taken into a 2M NaOH solution and extracted twice with diethyl ether. The combined ether portions were treated with brine, dried (Na2SO4), filtered, and the solvent was removed in vacuo to give the crude residue. The hydrochloride salt was made by dissolving the pure base in diethyl ether and adding an excess of an ethereal HCl solution to give a white solid. The salt was recrystallized twice from ethanol/diethyl ether to give 3.8 g (62% yield) Mp: 257°-8° C. [α]21D =-97.7° (C=0.1 CHCl3). The free base was made from the hydrochloride salt to give an oil. GC-MS (70 eV) M=301 (100%).

後処理

  1. additionadded dropwise under 1.5 h
  2. customThe solvent was removed in vacuo
  3. extractionextracted twice with diethyl ether
  4. additionThe combined ether portions were treated with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customto give the crude residue
  9. customto give a white solid
  10. customThe salt was recrystallized twice from ethanol/diethyl ether
  11. customto give 3.8 g (62% yield) Mp: 257°-8° C. [α]21D =-97.7° (C=0.1 CHCl3)
  12. customto give an oil

出典と根拠

ORDレコード
ord-26091e83879c49e796630f835fb52b94
出典データセット
uspto-grants-1997_04
特許番号
US05616610

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