Hydrochloric Acid → (2S)-1-allyloxycarbonyl-2-hydroxymethyl-4-methylenepyrrolidine

HRID 1090540ノート

反応式

HRID 1090540 の反応式
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C:10](=[CH2:12])[CH2:9][C@H:8]1[CH2:13][O:14][Si](C(C)(C)C)(C)C)=[O:6])[CH:2]=[CH2:3].Cl.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.[Cl-].[Na+].O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C:10](=[CH2:12])[CH2:9][C@H:8]1[CH2:13][OH:14])=[O:6])[CH:2]=[CH2:3]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 18639168(2S)-1-allyloxycarbonyl-2-(t-butyldimethylsilyloxymethyl)-4-methylenepyrrolidine

生成物 1

HCID 57149333(2S)-1-allyloxycarbonyl-2-hydroxymethyl-4-methylenepyrrolidine収率 97.6%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of (2S)-1-allyloxycarbonyl-2-(t-butyldimethylsilyloxymethyl)-4-methylenepyrrolidine (2.88 g) in ethyl acetate (100 ml) was added 6N hydrochloric acid (3.0 ml) at ambient temperature. After stirring for 1 hour at ambient temperature, to the mixture were added potassium carbonate (2.54 g) and brine (30 ml) with stirring. The organic layer was separated, washed in turn with aqueous sodium hydrogen carbonate and brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel (40 ml) eluting with a mixture of n-hexane and ethyl acetate (3:1 V/V) to give (2S)-1-allyloxycarbonyl-2-hydroxymethyl-4-methylenepyrrolidine (1.78 g).

後処理

  1. stirringwith stirring
  2. customThe organic layer was separated
  3. washwashed in turn with aqueous sodium hydrogen carbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel (40 ml)
  7. washeluting with a mixture of n-hexane and ethyl acetate (3:1 V/V)

出典と根拠

ORDレコード
ord-27574aa2f87f4c67869e37db7426cf59
出典データセット
uspto-grants-1992_01
特許番号
US05081237

反応ノート

読み込み中…