(2S)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione → (2S)-2-(hydroxymethyl)-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione

HRID 420692Notes

Reaction equation

HRID 420692 reaction equation
CC([Si](C)(C)[O:6][CH2:7][C@H:8]1[N:18]2[C:19]3[N:10]([C:11](=[O:21])[CH:12]=[CH:13][C:14]=3[N:15]=[CH:16][C:17]2=[O:20])[CH2:9]1)(C)C>CO>[OH:6][CH2:7][C@H:8]1[N:18]2[C:19]3[N:10]([C:11](=[O:21])[CH:12]=[CH:13][C:14]=3[N:15]=[CH:16][C:17]2=[O:20])[CH2:9]1

Participants

3

Reactant 1

HCID 58001742(2S)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione

Product 1

HCID 58001793(2S)-2-(hydroxymethyl)-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dioneYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of (2S)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione (42.6 g, 128 mmol) and Dowex 50X2-200 ion exchange resin (50 g, 128 mmol) in MeOH (1000 mL) was stirred at room temperature for 15 h. The reaction mixture was filtered to give (2S)-2-(hydroxymethyl)-1,2-dihydro-3H,8H-2a,5,8a-triazaacenaphthylene-3,8-dione (26.55 g, 121 mmol, 95%).

Workup

  1. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-48f6f014c9ce4bb6b096d0b1b5d0e2ec
Source dataset
uspto-grants-2012_01
Patent number
US08097628B2

Reaction notes

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