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

HRID 882341

反応式

HRID 882341 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 3776Isopropanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-132fd3fc5b8040e294e142504adef875
出典データセット
uspto-grants-2015_03
特許番号
US08993808B2

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