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

HRID 467037

반응식

HRID 467037 반응식
[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

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 110982704-Benzyloxy-3-methoxyphenylacetyl chloride2회HCID 143486951-(aminomethyl)-2,3-dihydro-1H-inden-1-ol2회

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-84d4541677c2490a87a383abbf65d849
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05158948

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