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

HRID 463742ノート

反応式

HRID 463742 の反応式
ClC(OCC)=O.[CH2:7]([N:14]1[C@H:18]([C:19](OC)=[O:20])[C@H:17]([C:23](O)=[O:24])[N:16]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:15]1=[O:33])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>O1CCCC1>[CH2:26]([N:16]1[C@H:17]2[CH2:23][O:24][C:19](=[O:20])[C@H:18]2[N:14]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:15]1=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 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 64.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of ethyl chloroformate (0.54 g) in tetrahydrofuran (2 ml) wasd added dropwise to a mixture of (4R,5S)-1,3-dibenzyl-5-methoxycarbonyl-2-oxoimidazolidine-4-carboxylic acid (mp., 149°-150° C., [α]36525 =-27.4° at c=1 in DMF, 1.84 g), triethylamine (0.51 g) and tetrahydrofuran (10 ml) at -5° C. The mixture was stirred at the same temperature for 30 minutes. Precipitated triethylamine hydrochloride was filtered off and the filtrate was added dropwise to a solution of sodium borohydride (0.24 g) in 90% aqueous tetrahydrofuran (10 ml) at -15° C. After reacting, the mixture was acidified with diluted hydrochloric acid and extracted with ethyl acetate. The extract was concentrated under reduced pressure and the residue was purified by chromatography on silica gel column to give (3aS,6aR)-1,3-dibenzylhexahydro-1H-furo[3,4-d]imidazole-2,4-dione (1.04 g). M.P., 114°-117° C. [α]D20 =+59.0° (c=1, CHCl3).

後処理

  1. filtrationPrecipitated triethylamine hydrochloride was filtered off
  2. additionthe filtrate was added dropwise to a solution of sodium borohydride (0.24 g) in 90% aqueous tetrahydrofuran (10 ml) at -15° C
  3. extractionextracted with ethyl acetate
  4. concentrationThe extract was concentrated under reduced pressure
  5. customthe residue was purified by chromatography on silica gel column

出典と根拠

ORDレコード
ord-f53204ee504d482b82870fde4eebbf6f
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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