1,8-Diazabicyclo(5.4.0)undec-7-ene → (R)-N-(5-bromo-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

HRID 42982

反応式

HRID 42982 の反応式
CC1(C)[C@@H]2CC[C@@]1(CS(O)(=O)=O)C(=O)C2.[Br:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[CH2:22][C@@H:21]([NH2:26])[CH2:20]2.C1CCN2C(=NCCC2)CC1.[CH3:38][CH:39]([S:41](Cl)(=[O:43])=[O:42])[CH3:40]>C(Cl)Cl.Cl>[Br:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[CH2:22][C@@H:21]([NH:26][S:41]([CH:39]([CH3:40])[CH3:38])(=[O:43])=[O:42])[CH2:20]2

参加物

6

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 824082-Propanesulfonyl chlorideHCID 46899975(R)-5-Bromo-2-aminoindan(1S)-(+)-10-camphorsulfonate

生成物 1

HCID 46899976(R)-N-(5-bromo-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide収率 87%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

(R)-5-bromo-2,3-dihydro-1H-inden-2-amine((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate (7.88 mmol, 3.5 g) was suspended in DCM (40 mL) and DBU (23.63 mmol, 3.53 mL, 3.60 g) was added. The mixture was purged with nitrogen and cooled in an ice bath before dropwise addition of propane-2-sulfonyl chloride (15.75 mmol, 1.760 mL, 2.246 g). Stirring was continued at 0° C. for 1 h before allowing to come to room temperature. The mixture was diluted with DCM (100 mL) and 1N HCl (100 mL) and the phases mixed and separated. The aqueous phase was further extracted with DCM (2×100 mL) before combined organics were washed with brine. Concentration gave a light yellow oil which was purified on silica eluting with 75% DCM/heptane then neat DCM. Desired fractions were collected and concentrated to give (R)—N-(5-bromo-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide as a colourless oil (2.18 g, 87%). 1H NMR (400 MHz, CDCl3) δ 1.39 (d, 6H) 2.88 (m, 2H) 3.17 (sept, 1H) 3.28 (m, 2H) 4.27 (m, 2H) 7.08 (d, 1H) 7.30 (d, 1H) 7.35 (s, 1H)

後処理

  1. customThe mixture was purged with nitrogen
  2. customto come to room temperature
  3. additionthe phases mixed
  4. customseparated
  5. extractionThe aqueous phase was further extracted with DCM (2×100 mL)
  6. washbefore combined organics were washed with brine
  7. concentrationConcentration
  8. customgave a light yellow oil which
  9. customwas purified on silica eluting with 75% DCM/heptane
  10. customDesired fractions were collected
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-243c4462bb5549778b19629d5237ff1f
出典データセット
uspto-grants-2013_09
特許番号
US08536214B2

関連ノート

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