Water → HCID 23287953, compound

HRID 1954123Notes

Reaction equation

HRID 1954123 reaction equation
[CH2:1]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]=[CH2:11].C[N+]1([O-])CC[O:23]CC1.ClCCl.[OH2:30]>CC(C)=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>[OH:30][CH:10]([CH2:11][OH:23])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:1][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=[O:18]

Participants

7

Reactant 4

HCID 962Water2×HCID 6344DichloromethaneHCID 82029Methyl morpholine oxideHCID 23295884HCID 23295884, compound

Product 1

HCID 23287953HCID 23287953, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 24489Sodium DithioniteCatalystHCID 180AcetoneSolvent

Procedure

To a mixture of N-(10-Undecenyl)-2-piperidone (4.00 g, 16 mmol) and a 60% aqueous solution of N-methylmorpholine-N-oxide (5 mL, 29 mmol) in water (10 mL) and acetone (20 mL) was added potassium osmate dihydrate (12 mg, 0.03 mmol). After stirring for 3 days, the mixture was treated with sodium dithionite (100 mg). After 30 minutes, dichloromethane (50 mL) and water (30 mL) were added and the organic layer separated. The aqueous layer was extracted with dichloromethane/10% methanol (2×70 mL). The combined organic extracts were dried over sodium sulfate and the solvents evaporated under vacuum. The residue was purified by chromatography using silica and ethyl acetate/methanol in a 0-20% gradient to yield 4.21 g (93%) N-(10,11-Dihydroxyundecyl)-2-piperidone (inventive compound no. 1617) as a colorless oil.

Workup

  1. waitAfter 30 minutes
  2. customthe organic layer separated
  3. extractionThe aqueous layer was extracted with dichloromethane/10% methanol (2×70 mL)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. customthe solvents evaporated under vacuum
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-0729860b93b44d89aa2cb83367264079
Source dataset
uspto-grants-2000_09
Patent number
US06121270

Reaction notes

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