(S)-(+)-N-(Boc)-2-methylpiperidine → HCID 12176154、化合物

HRID 1747103ノート

反応式

HRID 1747103 の反応式
[C:1]([N:8]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].I([O-])(=O)(=O)=[O:16].[Na+]>C(OCC)(=O)C.O.O.[Ru](=O)=O>[C:1]([N:8]1[C@@H:13]([CH3:14])[CH2:12][CH2:11][CH2:10][C:9]1=[O:16])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

参加物

6

反応物 2

HCID 11019870(S)-(+)-N-(Boc)-2-methylpiperidineHCID 23667635Sodium periodate

生成物 1

HCID 12176154HCID 12176154、化合物収率 59%

試薬・触媒・溶媒 3

HCID 16211523Ruthenium dioxide hydrate触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Ruthenium(IV) oxide hydrate (0.8 g, 0.006 mol) then a solution of N-BOC-6(S)-methyl-piperidine (4.00 g, 0.020 mol) in ethyl acetate (240 ml) were added to a solution of sodium periodate (21.36 g, 0.100 mole) in water (200 ml) and strongly stirred for 24 hours at room temperature under argon atmosphere. After separation the aqueous phase was extracted with ethyl acetate (3×100 ml). The combined organic phases were dried with magnesium sulfate and then treated with activated carbon, giving a colorless solution that was evaporated on a rotavapor at 30° C. The residue (3.98 g) was purified by silicagel (125 g) column chromatography with cyclohexane-ethyl acetate (1-1, v/v), furnishing a product (2.50 g, 59% yield) which according to its 1H-NMR spectrum was pure enough for the next reaction step.

後処理

  1. customAfter separation the aqueous phase
  2. extractionwas extracted with ethyl acetate (3×100 ml)
  3. dry with materialThe combined organic phases were dried with magnesium sulfate
  4. additiontreated with activated carbon
  5. customgiving a colorless solution that
  6. customwas evaporated on a rotavapor at 30° C
  7. customThe residue (3.98 g) was purified by silicagel (125 g) column chromatography with cyclohexane-ethyl acetate (1-1

出典と根拠

ORDレコード
ord-a0190b0be5604c1583bdb6e417bf05b1
出典データセット
uspto-grants-2015_10
特許番号
US09150558B2

反応ノート

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