Water → (RS)-1,1-Dimethylethyl 4-(1,2-Dihydroxyethyl)-4-(phenylmethoxymethyl)-1-piperidinecarboxylate

HRID 2213031Notes

Reaction equation

HRID 2213031 reaction equation
[CH:1]([C:3]1([CH2:16][O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=[CH2:2].C[N+]1([O-])CC[O:29]CC1.S([O-])(O)(=O)=O.[Na+].[OH2:39]>O1CCCC1.[Os](=O)(=O)(=O)=O>[OH:39][CH:1]([C:3]1([CH2:16][O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:13])[CH3:14])=[O:10])[CH2:5][CH2:4]1)[CH2:2][OH:29]

Participants

7

Reactant 4

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 516919Sodium BisulfateHCID 219553091,1-Dimethylethyl 4-Ethenyl-4-(phenylmethoxymethyl)-1-piperidinecarboxylate

Product 1

HCID 21955196(RS)-1,1-Dimethylethyl 4-(1,2-Dihydroxyethyl)-4-(phenylmethoxymethyl)-1-piperidinecarboxylateYield 96%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Osmium tetroxide (2.5 wt % solution in tert-butanol, 240 mL) was added to a mixture of 1,1-dimethylethyl 4-ethenyl-4-(phenylmethoxymethyl)-1-piperidinecarboxylate (Description 96, 1.01 g, 3 mmol) and N-methylmorpholine-N-oxide (460 mg, 4 mmol) in water (4 mL) and tetrahydrofuran (12 mL). The mixture was stirred at room temperature for 24 hours then saturated aqueous sodium hydrogen sulphate (5 mL) was added. The mixture was extracted with ethyl acetate (2×15 mL), the combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound (1.05 g, 96%). m/z (ES+) 366 (M+1).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×15 mL)
  2. dry with materialthe combined organic fractions were dried (MgSO4)
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3be7c58a40dd4f948d7aa7f17f8a93bc
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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