Hydrochloric Acid → (2S)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-4-oxo-pyrrolidine

HRID 1090539ノート

反応式

HRID 1090539 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:14][C:15]([N:17]1[CH2:21][C@H:20]([OH:22])[CH2:19][C@H:18]1[CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[O:16])[CH:12]=[CH2:13].Cl>ClCCl.C(OCC)(=O)C.[Cl-].[Na+].O.C(N(CC)CC)C>[CH2:11]([O:14][C:15]([N:17]1[CH2:21][C:20](=[O:22])[CH2:19][C@H:18]1[CH2:23][O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:26])[CH3:27])=[O:16])[CH:12]=[CH2:13]

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 18639173(2S,4R)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine

生成物 1

HCID 18639169(2S)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-4-oxo-pyrrolidine収率 90.6%

試薬・触媒・溶媒 4

HCID 6344Dichloromethane溶媒3 回HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
-70 °C

実験手順

To a solution of oxalyl chloride (0.18 ml) in dichloromethane (10 ml) was added dropwise a solution of dimethyl sulfoxide (0.3 ml) in dichloromethane (2 ml) at -60° C. After stirring at -70° C. for 30 minutes, to the mixture was added dropwise a solution of (2S,4R)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl-4-hydroxypyrrolidine (0.6 g) in dichloromethane (5 ml) at -60° C. After stirring at -70° C. for 30 minutes, to the mixture was added dropwise triethylamine (1.3 ml) and the resulting mixture was allowed to warm to 0° C. and diluted with ethyl acetate (150 ml) and brine. After adjusting pH to around 3 with 10% hydrochloric acid, the organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (50 ml) eluting with 15% ethyl acetate in hexane to give (2S)-1-allyloxycarbonyl-2-t-butyldimethylsilyloxymethyl- 4-oxo-pyrrolidine (0.54 g).

後処理

  1. stirringAfter stirring at -70° C. for 30 minutes, to the mixture
  2. temperatureto warm to 0° C.
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel (50 ml)
  8. washeluting with 15% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-30ba85f0573148e7bc7ebb9404c80e31
出典データセット
uspto-grants-1992_01
特許番号
US05081237

反応ノート

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