Sodium periodate → HCID 68499161, compound

HRID 1176236Notes

Reaction equation

HRID 1176236 reaction equation
[CH2:1]([O:4][CH:5]1[CH:10]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])=[CH:13][CH:12]=2)[CH2:9][CH2:8][N:7]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:6]1)[CH:2]=C.I([O-])(=O)(=O)=[O:39].[Na+]>[Os](=O)(=O)(=O)=O.O1CCCC1.O>[OH:39][CH2:2][CH2:1][O:4][CH:5]1[CH:10]([C:11]2[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][CH2:20][O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])=[CH:15][CH:16]=2)[CH2:9][CH2:8][N:7]([C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[CH2:6]1

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 68501888HCID 68501888, compound

Product 1

HCID 68499161HCID 68499161, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

8.54 g of tert-butyl 3-allyloxy-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate are initially charged in a 3:1 tetrahydrofuran/water mixture (52 ml) with stirring at room temperature and admixed with 2.07 ml of osmium tetroxide (2.5% by wt. in tert-BuOH). Subsequently, 9.00 g of sodium periodate are added in portions. The reaction mixture is stirred further over 2 hours. The reaction mixture is concentrated by evaporation. The residue is suspended in a 1:1 dichloromethane/methanol mixture (150 ml), cooled to 5° C. and admixed with 3.96 g of sodium borohydride in portions. The reaction mixture is stirred at 5° C. for 1.5 hours and subsequently concentrated by evaporation. The residue is stirred in 200 ml of dichloromethane, filtered through glass fibre filter and washed with dichloromethane. The filtrate is washed with a 1:1 brine/water mixture, filtered through cotton wool, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.17 (1:1 EtOAc-heptane). Rt=5.22.

Workup

  1. stirringThe reaction mixture is stirred further over 2 hours
  2. concentrationThe reaction mixture is concentrated by evaporation
  3. temperaturecooled to 5° C.
  4. stirringThe reaction mixture is stirred at 5° C. for 1.5 hours
  5. concentrationsubsequently concentrated by evaporation
  6. stirringThe residue is stirred in 200 ml of dichloromethane
  7. filtrationfiltered through glass
  8. filtrationfibre filter
  9. washwashed with dichloromethane
  10. washThe filtrate is washed with a 1:1 brine/water mixture
  11. filtrationfiltered through cotton wool
  12. dry with materialdried over sodium sulphate
  13. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-aaf84f704475464abe80251dfc6d8b7a
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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