Hydrochloric Acid → (1R,2S)-2-(4-(Benzyloxy)phenyl)cyclopropan-1-amine

HRID 882341

반응식

HRID 882341 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:17][C@@H:16]2[N+:18]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CC(O)C.[Zn]>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:15]2[CH2:17][C@H:16]2[NH2:18])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 2

HCID 313Hydrochloric AcidHCID 666295831-(benzyloxy)-4-((1R,2S)-2-nitrocyclopropyl)benzene

생성물 1

HCID 51888238(1R,2S)-2-(4-(Benzyloxy)phenyl)cyclopropan-1-amine수율 70%

시약·촉매·용매 2

HCID 23994Zinc촉매HCID 3776Isopropanol용매

실험 절차

Zn dust (1.97 g, 30 mol) was added in small portions, over a period of 30 min, to a vigorously stirred solution of 1-(benzyloxy)-4-[(1R,2S)-2-nitrocyclopropyl]benzene (0.81 g, 3.0 mmol) in i-PrOH (25 mL) and HCl (11 mL of aqueous solution 2.7 N, 30 mmol). After 17 h the mixture was filtered through a pad of celite, that was washed with 10 mL of methanol. The filtrate was concentrated and 10 mL of water were added, washing with CH2Cl2 (3×15 mL). The organic layers were dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the crude product was purified by column chromatography on silica gel (10% MeOH/CH2Cl2) affording 0.50 g of (trans)-2-[4-(benzyloxy)phenyl]cyclopropanamine [Rf=0.2 (10% MeOH/CH2Cl2), white solid, 70% yield]. 1H-NMR (MeOH, 250 MHz, δ): 7.45-7.27 (m, 5H, ArH); 6.96 (d, J=8.5 Hz, 2H, ArH); 6.86 (d, J=8.5 Hz, 2H, ArH); 5.03 (s, 2H, CH2); 2.41-2.34 (m, 1H, CH); 1.86-1.76 (m, 1H, CH); 0.98-0.85 (m, 2H, CH2).

후처리

  1. filtrationAfter 17 h the mixture was filtered through a pad of celite, that
  2. washwas washed with 10 mL of methanol
  3. concentrationThe filtrate was concentrated
  4. addition10 mL of water were added
  5. washwashing with CH2Cl2 (3×15 mL)
  6. dry with materialThe organic layers were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customAfter removal of the solvent
  9. customthe crude product was purified by column chromatography on silica gel (10% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-132fd3fc5b8040e294e142504adef875
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08993808B2

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