Acetone → Tert-butyl (1-(2-(7-(1,2-dihydroxyethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

HRID 1041971Notes

Reaction equation

HRID 1041971 reaction equation
C(C1[CH:8]=[CH:7][N:6]2[C:9]([C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[C:15]([N:22]5[CH2:27][CH2:26][CH:25]([CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:24][CH2:23]5)[CH:16]=[CH:17][CH:18]=4)[N:13]=3)=[N:10][N:11]=[C:5]2[CH:4]=1)=C.C[N+]1([O-])CC[O:41]CC1.[CH3:45][C:46]([CH3:48])=[O:47]>O=[Os](=O)(=O)=O>[OH:47][CH:46]([C:48]1[CH:8]=[CH:7][N:6]2[C:9]([C:12]3[CH:21]=[CH:20][C:19]4[C:14](=[C:15]([N:22]5[CH2:27][CH2:26][CH:25]([CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:24][CH2:23]5)[CH:16]=[CH:17][CH:18]=4)[N:13]=3)=[N:10][N:11]=[C:5]2[CH:4]=1)[CH2:45][OH:41]

Participants

5

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 86654348Tert-butyl (1-(2-(7-vinyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

Product 1

HCID 86654349Tert-butyl (1-(2-(7-(1,2-dihydroxyethyl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To tert-butyl (1-(2-(7-vinyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yl)piperidin-4-yl)methylcarbamate (68 mg, 0.14 mmol) in acetone (2 mL) was added OsO4 (178 mg, 0.014 mmol) (2% in tBuOH) and NMO (49 mg, 0.21 mmol) (50% in H2O). The reaction was then stirred for 2 hours, then concentrated and purified by flash column chromatography (20:1 Hexane/EtOAc), affording the desired product.

Workup

  1. concentrationconcentrated
  2. custompurified by flash column chromatography (20:1 Hexane/EtOAc)

Sources & evidence

ORD record
ord-3ab5afc127d641fcb2821681ac91d3db
Source dataset
uspto-grants-2013_10
Patent number
US08557809B2

Reaction notes

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