Hydrochloric Acid → (2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol

HRID 1650276노트

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HRID 1650276 반응식
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:9][C@H:8]1[C:17](OC)=[O:18])=[O:6])[CH:2]=[CH2:3].O1CCCC1.[BH4-].[Na+].Cl>C(O)C.C(OCC)(=O)C.O>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][S:13]([CH3:16])(=[O:14])=[O:15])[CH2:9][C@H:8]1[CH2:17][OH:18])=[O:6])[CH:2]=[CH2:3]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 10733517(2S,4R)-N-allyloxycarbonyl-4-methanesulfonyloxyproline methyl ester

생성물 1

HCID 18639172(2S,4R)-1-allyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol수율 88.8%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
-60 °C

실험 절차

To a solution of (2S,4R)-1-allyloxycarbonyl-2-methoxycarbonyl-4-methanesulfonyloxypyrrolidine (281 g) in a mixture of ethanol (0.9 () and tetrahydrofuran (0.6 l) was added sodium borohydride (69.2 g) at 5° C. and the resulting mixture was allowed to stir for 3.5 hours at 20°-27° C. After cooling to -60° C., the reaction mixture was taken up into a mixture of 12N hydrochloric acid (152.4 ml), water (2.5 l) and ethyl acetate (2.5 l) at 0° C. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2 l). The organic layer and the extract were combined, washed with 2 portions of brine (500 ml×2 ), dried over magnesium sulfate and evaporated to give (2S,4R)-1-allyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine (226.9 g).

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2 l)
  3. washwashed with 2 portions of brine (500 ml×2 )
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

출처 및 근거

ORD 기록
ord-f0109632e5e0473f87e2011b3384e03e
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04923857

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