Sodium Sulfite → ((R)-2-Hydroxy-4-oxo-butyl)-carbamic Acid benzyl ester

HRID 1096293노트

반응식

HRID 1096293 반응식
[CH2:1]([O:8][C:9](=[O:17])[NH:10][CH2:11][C@H:12]([OH:16])[CH2:13][CH:14]=C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:22]CC1.I([O-])(=O)(=O)=O.[Na+].S([O-])([O-])=O.[Na+].[Na+]>CC(C)=O.C1COCC1.O.[Os](=O)(=O)(=O)=O>[CH2:1]([O:8][C:9](=[O:17])[NH:10][CH2:11][C@H:12]([OH:16])[CH2:13][CH:14]=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 66783125((R)-2-Hydroxy-pent-4-enyl)-carbamic Acid benzyl ester

생성물 1

HCID 86638392((R)-2-Hydroxy-4-oxo-butyl)-carbamic Acid benzyl ester수율 133%

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 21553975Acetone water tetrahydrofuran용매

실험 절차

A mixture of ((R)-2-hydroxy-pent-4-enyl)-carbamic acid benzyl ester (690 mg, 2.35 mmol), osmium(VIII) oxide (4% solution in water, 0.22 mL, 35 μmol), and 4-methyl-morpholine-4-oxide (50% solution in water, 0.27 mL, 1.29 mmol) in acetone/THF/water 6:2:1 (6 mL) was stirred for 45 min at RT, then sodium metaperiodate (1.51 g, 7.04 mmol) was added, then after 16 h 10% aq. sodium sulfite solution (5.5 mL) was added. The reaction mixture was partitioned between EtOAc and water, the organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane-EtOAc gradient) produced the title compound (407 mg, 73%) as a brown gum.

후처리

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. washthe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

출처 및 근거

ORD 기록
ord-65826cdb9b344186a7cc0f84e8f39e26
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138175B2

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