Methanol → HCID 59515669, compound

HRID 1161194Notes

Reaction equation

HRID 1161194 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]([CH2:15][C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:9]2=[O:14])([O-])=O.CO>>[NH2:1][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:8]([CH2:15][C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:9]2=[O:14]

Participants

3

Reactant 2

HCID 887MethanolHCID 59515814HCID 59515814, compound

Product 1

HCID 59515669HCID 59515669, compound

Procedure

Into a round bottom flask was combined (S)-tert-butyl 2-((5-nitro-1-oxoisoquinolin-2(1H)-yl)methyl)pyrrolidine-1-carboxylate (1.54 g, 0.00412 mol) palladium on C (0.04 g, 0.0004 mol) and methanol (60 mL, 1 mol). The flask was purged and evacuated three times with hydrogen. The mixture was allowed to stir at room temperature under 1 atm for three hours. The mixture was filtered over a bed of celite and the filtrate was reduced in vacuo to yield a light brown oil which was purified by column chromatography on silica gel using a methylene chloride:methanol (0-10%) gradient. The combined pure fractions were reduced in vacuo to yield a tan solid.

Workup

  1. customInto a round bottom flask was combined
  2. customThe flask was purged
  3. customevacuated three times with hydrogen
  4. filtrationThe mixture was filtered over a bed of celite
  5. customto yield a light brown oil which
  6. customwas purified by column chromatography on silica gel using a methylene chloride
  7. customto yield a tan solid

Sources & evidence

ORD record
ord-71311c64b10d4f98b1cc88dfef91f01c
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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