Acetone → tert-Butyl 3,4-dihydroxypiperidine-1-carboxylate

HRID 712495Notes

Reaction equation

HRID 712495 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])CCC=[CH:3][CH2:2]1.C[N+]1([O-])CC[O:18]CC1.OS([O-])=O.[Na+].[CH3:27][C:28]([CH3:30])=[O:29]>C(O)(C)C.O=[Os](=O)(=O)=O>[OH:29][CH:28]1[CH:30]([OH:18])[CH2:3][CH2:2][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:27]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 13094787tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylateHCID 23665763Sodium Bisulfite

Product 1

HCID 22929427tert-Butyl 3,4-dihydroxypiperidine-1-carboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 3776IsopropanolSolvent

Procedure

To a mixture of tert-butyl 5,6-dihydropyridine-1(2H)-carboxylate (2.40 g, 13.10 mmol, 1 eq) and NMO (2.65 g, 19.60 mmol, 1.5 eq) in acetone (60 mL) was added a solution of OsO4 (20 mg) in isopropanol (5 mL). The mixture was stirred overnight at room temperature. To this, 10 mL of saturated NaHSO3 aqueous solution was added dropwise, the reaction mixture was stirred for 0.5 h at room temperature and concentrated in vacuo. The pH was adjusted to 5-6 by adding dilute hydrochloric acid. The organic phase was extracted with CH2Cl2 (50 mL×2), dried over anhydrous Na2SO4 and concentrated in vacuo to give the title compound as colorless oil (2.60 g, 92.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 218.2 (M+1).

Workup

  1. stirringthe reaction mixture was stirred for 0.5 h at room temperature
  2. concentrationconcentrated in vacuo
  3. additionby adding dilute hydrochloric acid
  4. extractionThe organic phase was extracted with CH2Cl2 (50 mL×2)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4ce464260c5640b9b69ffccf51040e4b
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

Loading…