Water → HCID 86725271, compound

HRID 1478877Notes

Reaction equation

HRID 1478877 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][C:7]2=[N:8][CH:9]=1)[CH:2]=[CH2:3].C[N+]1([O-])CC[O:24]CC1.[OH2:28]>C(O)(C)(C)C.CCOCC.[Os](=O)(=O)(=O)=O>[OH:28][CH:2]([CH2:3][OH:24])[CH2:1][C:4]1[CH:5]=[C:6]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][C:7]2=[N:8][CH:9]=1

Participants

7

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 86725270HCID 86725270, compound

Product 1

HCID 86725271HCID 86725271, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 3283Diethyl EtherSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of tert-butyl 3-allyl-5,7-dihydropyrrolo[3,4-b]pyridine-6-carboxylate (430 mg, 1.64 mmol) in tert-butanol (5 mL) and water (5 mL) was added N-methyl-morpholine N-oxide (422 mg, 3.6 mmol) followed by osmium tetroxide (20 μl, 4% aqueous solution). The resulting solution was stirred for 48 hr then diluted with ether, washed with 10% sodium thiosulphate solution and brine, dried over magnesium sulfate and concentrated to give the title compound as a solid.

Workup

  1. washwashed with 10% sodium thiosulphate solution and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1ad73cdb53574f9aa10a95fb8b37ed50
Source dataset
uspto-grants-2016_08
Patent number
US09403850B2

Reaction notes

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