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

HRID 467037

反応式

HRID 467037 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 19813063N-(4-Benzyloxy-3-methoxyphenylacetyl)-1-aminomethyl-1-hydroxyindan収率 82.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-84d4541677c2490a87a383abbf65d849
出典データセット
uspto-grants-1992_10
特許番号
US05158948

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