Methyl morpholine oxide → Tert-butyl 4-(2,3-dihydroxypropyl)-4-hydroxy-1-piperidinecarboxylate

HRID 47323ノート

反応式

HRID 47323 の反応式
[CH2:1]([C:4]1([OH:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].C[N+]1([O-])CC[O:22]CC1.O1CCCC1.[OH2:31]>C(O)(C)(C)C.[Os](=O)(=O)(=O)=O>[OH:31][CH:2]([CH2:3][OH:22])[CH2:1][C:4]1([OH:17])[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1

参加物

6

反応物 3

HCID 82029Methyl morpholine oxideHCID 21881883Oxolane--water (1/1)HCID 21955339Tert-butyl 4-allyl-4-hydroxypiperidine-1-carboxylate

生成物 1

HCID 22744545Tert-butyl 4-(2,3-dihydroxypropyl)-4-hydroxy-1-piperidinecarboxylate

試薬・触媒・溶媒 2

HCID 30318Osmium Tetroxide触媒HCID 6386tert-Butanol溶媒

実験手順

9.83 g of tert-butyl 4-allyl-4-hydroxy-1-piperidinecarboxylate was dissolved in 60 ml tetrahydrofuran/water (9:1), a solution (2.5 wt %, 2 ml) of osmium tetraoxide in tert-butyl alcohol and 6.68 g of N-methylmorpholine-N-oxide were added thereto, and the mixture was stirred at room temperature overnight. The reaction solution was evaporated, and the resulting residue was partitioned into ethyl acetate and water, washed with brine and dried over magnesium sulfate. After filtration, the solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give 9.11 g of tert-butyl 4-(2,3-dihydroxypropyl)-4-hydroxy-1-piperidinecarboxylate.

後処理

  1. customThe reaction solution was evaporated
  2. customthe resulting residue was partitioned into ethyl acetate and water
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated
  7. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/methanol)

出典と根拠

ORDレコード
ord-275fc92239a847d19c1f96b3353e7516
出典データセット
uspto-grants-2004_03
特許番号
US06699870B2

反応ノート

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