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

HRID 463739ノート

反応式

HRID 463739 の反応式
[CH2:1]([N:8]1[C@@H:12]([C:13](OC)=[O:14])[C@@H:11]([C:17](O)=[O:18])[N:10]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:9]1=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C)C.[BH4-].[Na+].Cl>O1CCCC1.O.C(Cl)(Cl)Cl>[CH2:20]([N:10]1[C@H:11]2[CH2:17][O:18][C:13](=[O:14])[C@H:12]2[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]1=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 4311764Sodium borohydrideHCID 11152843(4S,5R)-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 97.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of (4S,5R)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (mp., 149°-150° C., [α]36525 =-27.7° at c=1 in DMF, 368 mg) in tetrahydrofuran (3 ml) and isopropanol (0.50 g) was added dropwise to a mixture of sodium borohydride (100 mg) and tetrahydrofuran (3 ml) at 5°-10° C. The obtained mixture was allowed to warm up to room temperature and to react at the same temperature for 5 hours. Then, 1N hydrochloric acid (10 ml) was added dropwise to the reaction mixture. The mixture was stirred at 55°-60° C. for 30 minutes. Chloroform (30 ml) and water (30 ml) were added to the mixture. Aqueous layer was separated from organic layer and extracted once with chloroform. The organic layers were combined, washed successively with water, 5% aqueous sodium hydrogen carbonate and water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give (3aS,6aR)-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4-dione (314 mg). M.P., 116°-117° C. [α]D25 =+61.1° (c=1, CHCl3).

後処理

  1. customto react at the same temperature for 5 hours
  2. customAqueous layer was separated from organic layer
  3. extractionextracted once with chloroform
  4. washwashed successively with water, 5% aqueous sodium hydrogen carbonate and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-c162bc0ac76344ccb24b96e5fcf10004
出典データセット
uspto-grants-1985_10
特許番号
US04544635

反応ノート

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