Acetone → HCID 14771965, compound

HRID 1366439Notes

Reaction equation

HRID 1366439 reaction equation
[N:1]1([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])CC=C[CH2:2]1.C[N+]1([O-])CC[O:20]CC1.[CH3:24][C:25]([CH3:27])=[O:26]>O.O=[Os](=O)(=O)=O>[OH:26][C@H:25]1[C@@H:27]([OH:20])[CH2:2][N:1]([C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])[CH2:24]1

Participants

6

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 643471Benzyl 3-pyrroline-1-carboxylate

Product 1

HCID 14771965HCID 14771965, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

Phenylmethyl 2,5-dihydro-1H-pyrrole-1-carboxylate (commercially-available) (5.07 g, 25 mmol) was dissolved in a mixture of acetone (25 mL) and water (10 mL). NMO (5.9 g, 50 mmol) was added followed by catalytic OsO4. The reaction was stirred for 19 hours and then quenched by the addition of an aqueous solution of Na2S2O3. A standard work-up followed by silica gel chromatography (3:1 Hexane:ethyl acetate to pure ethyl acetate to 9:1 DCM: MeOH) yielded phenylmethyl (cis)-3,4-dihydroxy-1-pyrrolidinecarboxylate (0.872 g, 15%) as a clear oil. LCMS: (M+H)+: 237.9.

Workup

  1. customquenched by the addition of an aqueous solution of Na2S2O3

Sources & evidence

ORD record
ord-4bb5283d5ace4ef5a4f177bf3e933c4c
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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