Sodium Sulfite → 3-[8-Chloro-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-1-(hydroxymethyl)cyclobutanol

HRID 386268Notes

Reaction equation

HRID 386268 reaction equation
[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:27]3[CH2:30][C:29](=[CH2:31])[CH2:28]3)=[N:9][C:10]=2[C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.C[N+]1([O-])CC[O:36]CC1.[O-]S([O-])=O.[Na+].[Na+].C1COCC1.[OH2:51]>CCOC(C)=O>[Cl:1][C:2]1[C:3]2[N:4]([C:8]([CH:27]3[CH2:30][C:29]([CH2:31][OH:36])([OH:51])[CH2:28]3)=[N:9][C:10]=2[C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 21881883Oxolane--water (1/1)HCID 536290387-(8-Chloro-3-(3-methylenecyclobutyl)imidazo[1,5-a]pyrazin-1-yl)-2-phenylquinoline

Product 1

HCID 536290393-[8-Chloro-1-(2-phenylquinolin-7-yl)imidazo[1,5-a]pyrazin-3-yl]-1-(hydroxymethyl)cyclobutanol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-[8-chloro-3-(3-methylenecyclobutyl)imidazo[1,5-a]pyrazin-1-yl]-2-phenylquinoline (3.2 g, 7.6 mmol) in THF-water mixture (100 mL, 3:1) were added NMO (1.94 g, 8.3 mmol) and potassium osmate dihydrate (0.14 g, 0.4 mmol). The reaction mixture was stirred at rt. After 20 h the reaction was quenched with Na2SO3 (4.8 g, 38 mmol). The reaction mixture was diluted with EtOAc (250 mL) and washed with brine (2×100 mL). Part of the solvent was removed and the organic phase was passed through celite, dried over anhydrous Na2SO4 and concentrated in vacuo. The material was carried on to the subsequent oxidation without further purification.

Workup

  1. washwashed with brine (2×100 mL)
  2. customPart of the solvent was removed
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe material was carried on to the subsequent oxidation without further purification

Sources & evidence

ORD record
ord-fa44abd282d141259f9d2c5daec9f52a
Source dataset
uspto-grants-2013_02
Patent number
US08367826B2

Reaction notes

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