Acetone → HCID 58382448, compound

HRID 1628041Notes

Reaction equation

HRID 1628041 reaction equation
C([C:4]1[N:5]=[C:6]2[C:12]([CH2:13][CH3:14])=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4([CH3:26])[O:25][CH2:24][CH2:23][O:22]4)=[CH:17][CH:16]=3)[N:10]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:7]2=[N:8][CH:9]=1)C=C.C[N+]1([O-])CC[O:39]CC1.[CH3:43][C:44]([CH3:46])=[O:45]>O.CC(O)(C)C>[CH2:13]([C:12]1[C:6]2[C:7](=[N:8][CH:9]=[C:4]([CH2:43][CH:44]([OH:45])[CH2:46][OH:39])[N:5]=2)[N:10]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:11]=1[C:15]1[CH:20]=[CH:19][C:18]([C:21]2([CH3:26])[O:25][CH2:24][CH2:23][O:22]2)=[CH:17][CH:16]=1)[CH3:14]

Participants

6

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 58382309HCID 58382309, compound

Product 1

HCID 58382448HCID 58382448, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolCatalystHCID 962WaterSolvent

Procedure

2-Allyl-7-ethyl-6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine (0.323 g, 0.673 mmol, Preparation #14) in acetone (9 mL) and water (1 mL) was treated with NMO (0.083 g, 0.707 mmol) and 2.5 wt % OSO4 in t-BuOH (0.42 mL, 0.034 mmol). The mixture was stirred at rt for about 1.5 h. The mixture was concentrated under reduced pressure and then the material was purified using a 10 g silica column with 95:5 DCM/MeOH as an eluent to give 3-(7-ethyl-6-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl)propane-1,2-diol (0.21 g, 61%): LC/MS (Table 2, Method b) Rt=2.55 min; MS m/z 514 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe material was purified

Sources & evidence

ORD record
ord-ec9e5b64228d4a1ba352810d449b1392
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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