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

HRID 1096293ノート

反応式

HRID 1096293 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 21553975Acetone water tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-65826cdb9b344186a7cc0f84e8f39e26
出典データセット
uspto-grants-2012_03
特許番号
US08138175B2

反応ノート

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