Stannous chloride dihydrate → (1R)-5-Bromo-2,3-dihydro-1H-inden-1-amine

HRID 1913403노트

반응식

HRID 1913403 반응식
[N:1]([C@H:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:13])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)=[N+]=[N-].O.O.Cl[Sn]Cl>CO>[Br:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[C@H:4]([NH2:1])[CH2:5][CH2:6]2

참가 물질

4

반응물 2

HCID 61436Stannous chloride dihydrateHCID 59179602(R)-1-azido-5-bromo-indane

생성물 1

HCID 28206722(1R)-5-Bromo-2,3-dihydro-1H-inden-1-amine수율 80.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of (R)-1-azido-5-bromo-indane (14.0 g, 58.8 mmol) was dissolved in methanol (150 mL) and was treated with SnCl2.2H2O (23.0 g, 106 mmol). The mixture was stirred at room temperature overnight (TLC indicated no starting material) and was concentrated to dryness. The resulting residue was treated with 2N aqueous NaOH (300 mL) and was extracted with EtOAc (2×300 mL). The combined organic extracts were washed with 1N HCl followed by water (2 L). The pH of the combined aqueous layers was adjusted to 11 with cold saturated NaOH solution and the mixture was extracted with EtOAc (2×300 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated to give 10.0 g (80%) of (1R)-5-bromoindan-1-amine as a dark yellow oil which solidified upon refrigeration. MS (ES+) 213.9 (M+H)+. 1H NMR (CDCl3) δ 1.70-1.75 (m, 1H), 2.40-2.45 (m, 1H), 2.77-2.82 (m, 1H), 2.93-2.97 (m, 1H), 4.28-4.33 (m, 1H), 7.18-7.23 (m, 1H), 7.36-7.41 (m, 2H).

후처리

  1. concentrationwas concentrated to dryness
  2. additionThe resulting residue was treated with 2N aqueous NaOH (300 mL)
  3. extractionwas extracted with EtOAc (2×300 mL)
  4. washThe combined organic extracts were washed with 1N HCl
  5. extractionthe mixture was extracted with EtOAc (2×300 mL)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6f3294ae9fdd4aff8e0c7b81140f9486
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609680B2

반응 노트

불러오는 중…