Sodium Bicarbonate → N-(4-Benzyloxy-3-methoxyphenylacetyl)-1-aminomethyl-1-hydroxyindan

HRID 467037

Reaktionsgleichung

Reaktionsgleichung von HRID 467037
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](Cl)=[O:17])=[CH:11][C:10]=1[O:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[NH2:26][CH2:27][C:28]1([OH:37])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29]1>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:26][CH2:27][C:28]2([OH:37])[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH2:30][CH2:29]2)=[O:17])=[CH:11][C:10]=1[O:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 110982704-Benzyloxy-3-methoxyphenylacetyl chloride2×HCID 143486951-(aminomethyl)-2,3-dihydro-1H-inden-1-ol2×

Produkt 1

HCID 19813063N-(4-Benzyloxy-3-methoxyphenylacetyl)-1-aminomethyl-1-hydroxyindanAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 4-benzyloxy-3-methoxyphenylacetyl chloride (18 mmol), the product of Example 4, in 50 mL of methylene chloride was added 50 mL of saturated aqueous sodium bicarbonate solution, followed by a solution of 1-aminomethyl-1-hydroxyindan (3.15 g, 19 mmol), the product of Example 1, in 20 mL of methylene chloride. The resulting two-phase mixture was stirred vigorously at ambient temperature for 2 hours. The aqueous and organic phases were separated and the aqueous phase was extracted with methylene chloride (75 mL). The combined organic layers were washed with 100 mL of 1M aqueous hydrochloric acid solution, dried over anhydrous magnesium sulfate, filtered and concentrated to give a yellow oil. The oil was purified by flash chromatography on silica gel eluting with 1:1 ethyl acetate/methylene chloride to give 6.17 g (82% yield) of the title compound as a white solid; 1H NMR (CDCl3).δ.1.96-2.08 (m, 1H), 2.18-2.28 (m, 1 H), 2.67-2.80 (m, 1H), 2.87-2.98 (m, 1H), 3.29-3.37 (m, 2H), 3.53-3.65 (m, 3H), 3.88 (s, 3H), 5.16 (s, 2H), 5.80-5.88 (m, 1H), 6.71 (dd, 1H, J=8.7, 3.0 Hz), 6.79 (d, 1H, J=3.0 Hz), 6.85 (d, 1H, J=8.7 Hz), 7.10-7.47 (m, 9H).

Aufarbeitung

  1. customThe aqueous and organic phases were separated
  2. extractionthe aqueous phase was extracted with methylene chloride (75 mL)
  3. washThe combined organic layers were washed with 100 mL of 1M aqueous hydrochloric acid solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow oil
  8. customThe oil was purified by flash chromatography on silica gel eluting with 1:1 ethyl acetate/methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-84d4541677c2490a87a383abbf65d849
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05158948

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