Ammonium formate → 1-(4,4-Dimethoxy-butyl)-3-hydroxy-imidazolidin-2-one

HRID 251006ノート

反応式

HRID 251006 の反応式
C([O:8][N:9]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][CH:17]([O:20][CH3:21])[O:18][CH3:19])[C:10]1=[O:22])C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.[Pd]>[CH3:21][O:20][CH:17]([O:18][CH3:19])[CH2:16][CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][N:9]([OH:8])[C:10]1=[O:22]

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 672725081-Benzyloxy-3-(4,4-dimethoxy-butyl)-imidazolidin-2-one

生成物 1

HCID 672723451-(4,4-Dimethoxy-butyl)-3-hydroxy-imidazolidin-2-one収率 66%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

To a solution of 1-Benzyloxy-3-(4,4-dimethoxy-butyl)-imidazolidin-2-one (1.61 g, 5.22 mmol) in EtOH (50 mL) was added ammonium formate (3.34 g, 52.9 mmol) and 10 wt % Pd/C (50% wet with water, 800 mg) and the mixture was stirred at room temperature for 2 hours. The mixture was vacuum filtered through celite and the cake was washed with EtOH. The solvent was removed from the filtrate under reduced pressure and the thus obtained solid was partitioned between water (10 mL) and CH2Cl2 (50 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×10 mL). The combined organic extracts were dried (Na2SO4) and concentrated. Purification of the crude material by column chromatography on silica gel (100% EtOAc) provided 0.75 g (66%) of 1-(4,4-Dimethoxy-butyl)-3-hydroxy-imidazolidin-2-one as a colorless oil. ES-MS m/z 241 (M+Na).

後処理

  1. filtrationfiltered through celite
  2. washthe cake was washed with EtOH
  3. customThe solvent was removed from the filtrate under reduced pressure
  4. customthe thus obtained solid was partitioned between water (10 mL) and CH2Cl2 (50 mL)
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with CH2Cl2 (3×10 mL)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. concentrationconcentrated
  9. customPurification of the crude material by column chromatography on silica gel (100% EtOAc)

出典と根拠

ORDレコード
ord-61809e737566463f829330d5f8a38c37
出典データセット
uspto-grants-2011_01
特許番号
US07863293B2

反応ノート

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