Water → HCID 23287953, compound

HRID 361509Notes

Reaction equation

HRID 361509 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-f916e72b58e547f1ae512b8806338a62
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

Loading…