Isopropanol → HCID 58478452, compound

HRID 1516374Notes

Reaction equation

HRID 1516374 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:19][CH2:20][CH:21]=C)[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].CC([OH:26])C>O.O=[Os](=O)(=O)=O>[CH2:1]([O:3][C:4]([C:6]1([CH2:19][CH2:20][CH:21]=[O:26])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 3776IsopropanolHCID 58478433HCID 58478433, compound

Product 1

HCID 58478452HCID 58478452, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

4-But-3-enyl-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (13.5 g, 43.48 mmol, 1 eq) was dissolved in i-PrOH (217 mL) and a solution of NaIO4 (20.23 g, 94.6 mmol, 2.18 eq) in 217 mL of water was added followed by OsO4 (37 mg, 0.144 mmol, 0.003 eq). The reaction mixture was vigorously stirred for 6 h. The reaction mixture was then quenched with 1500 mL of water, transferred to a separatory funnel and extracted with ethyl acetate (3×200 mL). The combined organics were dried over Na2SO4 and purified by column chromatography on silica gel (300 g column, 30% EtOAc in heptanes; 50 mL/min). This gave 8.5 g (63%) of the title compound as a beige oil.

Workup

  1. customThe reaction mixture was then quenched with 1500 mL of water
  2. customtransferred to a separatory funnel
  3. extractionextracted with ethyl acetate (3×200 mL)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. custompurified by column chromatography on silica gel (300 g column, 30% EtOAc in heptanes; 50 mL/min)

Sources & evidence

ORD record
ord-edaab4338f094241837ec67d22cfed61
Source dataset
uspto-grants-2012_07
Patent number
US08227481B2

Reaction notes

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