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

HRID 1090540노트

반응식

HRID 1090540 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-27574aa2f87f4c67869e37db7426cf59
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05081237

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