Hydrochloric Acid → (3AS,6aR)-1,3-dibenzyltetrahydro-1H-furo(3,4-d)imidazole-2,4-dione

HRID 2413396ノート

反応式

HRID 2413396 の反応式
[BH4-].[Na+].[CH2:3]([N:10]1[C@H:14]([C:15](OC)=[O:16])[C@H:13]([C:19](O)=[O:20])[N:12]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:11]1=[O:29])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl-].[Ca+2].[Cl-].Cl>C(O)C>[CH2:22]([N:12]1[C@H:13]2[CH2:19][O:20][C:15](=[O:16])[C@H:14]2[N:10]([CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:11]1=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 11428617(4R,5S)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid

生成物 1

HCID 119819(3AS,6aR)-1,3-dibenzyltetrahydro-1H-furo(3,4-d)imidazole-2,4-dione収率 81.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒3 回

実験手順

To a mixture of sodium borohydride (0.55 g) and 99.5% ethanol (20 ml) were added dropwise a solution of (4R,5S)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (mp., 149°-150° C., [α]365b =-27.7 ° at c=1 in DMF, 2.00 g) in 99.5% ethanol (30 ml) at 0°-5° C. and a solution of anhydrous calcium chloride (0.80 g) in 99.5% ethanol (8 ml) at the same temperature. The obtained mixture was allowed to warm up to room temperature and to react at the same temperature for 18 hours under stirring. Then, 1N hydrochloric acid was added dropwise to the reaction mixture. The solvent was removed from the mixture at 50°-55° C. under reduced pressure. The residue was shaken with chloroform (50 ml) and water (50 ml). Chloroform layer was washed successively with 5% aqueous sodium hydrogen carbonate and water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was treated with ether (10 ml), filtered and dried to give (3aS,6aR)-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4-dione (1.43 g). M.P., 116°-117° C. [α]D25 =+60.9° (c=1, CHCl3).

後処理

  1. customto react at the same temperature for 18 hours
  2. customThe solvent was removed from the mixture at 50°-55° C. under reduced pressure
  3. stirringThe residue was shaken with chloroform (50 ml) and water (50 ml)
  4. washChloroform layer was washed successively with 5% aqueous sodium hydrogen carbonate and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionThe residue was treated with ether (10 ml)
  8. filtrationfiltered
  9. customdried

出典と根拠

ORDレコード
ord-ca7e8d6d4a0a4082a49625806e836231
出典データセット
uspto-grants-1985_01
特許番号
US04496739

反応ノート

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