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

HRID 2300159노트

반응식

HRID 2300159 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 6386tert-Butanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4eb4ea90dcb64690ae507c2e0db255d6
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498159B1

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