Hydrochloric Acid → (3aR,6aS)-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4-dione

HRID 463738노트

반응식

HRID 463738 반응식
[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.[BH4-].[Na+].Cl>C1(C)C=CC=CC=1.C(O)(C)C>[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

참가 물질

6

반응물 3

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

생성물 1

HCID 11427250(3aR,6aS)-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4-dione수율 93.5%

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 3776Isopropanol용매

실험 절차

A solution of (4R,5S)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (mp., 149°-150° C., [α]36525 =+27.7° at c=1.0 in DMF, 368 mg) in toluene (2 ml) and isopropanol (3 ml) was added dropwise to a suspension of sodium borohydride (100 mg) in toluene at 5°-10° C. The obtained mixture was allowed to warm up to room temperature and to react at the same temperature for 18 hours. Then, 1N hydrochloric acid (10 ml) was added dropwise to the mixture. The mixture was stirred at 55°-60° C. for 30 minutes. Aqueous layer was separated from organic layer and extracted once with toluene (15 ml). The organic layers were combined, washed successively with water, 5% aqueous sodium hydrogen carbonate and water, dried over anhydrous magnesium sulfate and concentrated to give (3aR,6aS)-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4-dione (301 mg). M.P., 116°-118° C. [α]D25 =-61.8° (c=1, CHCl3).

후처리

  1. customto react at the same temperature for 18 hours
  2. customAqueous layer was separated from organic layer
  3. extractionextracted once with toluene (15 ml)
  4. washwashed successively with water, 5% aqueous sodium hydrogen carbonate and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-7132a57822484d77bc4744d10d522e3f
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04544635

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