Methanol → HCID 59515814, compound

HRID 1161193Notes

Reaction equation

HRID 1161193 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7]O[C:9]2=[O:14])([O-:3])=[O:2].[NH2:15][CH2:16][C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].CO>>[N+:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][N:15]([CH2:16][C@@H:17]1[CH2:21][CH2:20][CH2:19][N:18]1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:9]2=[O:14])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1512533tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylateHCID 100127605-nitro-1H-isochromen-1-one

Product 1

HCID 59515814HCID 59515814, compound

Procedure

Into a round bottom flask was combined 5-nitro-isochromen-1-one (3.50 g, 0.0165 mol), (S)-tert-butyl 2-(aminomethyl)pyrrolidine-1-carboxylate (4.12 g, 0.0206 mol) and methanol (100.0 mL, 2.469 mol). The mixture was heated at reflux for 2 hours. The mixture was allowed to cool and the volatiles were removed under reduced pressure. The crude oil was chromatographed using a methylene chloride:methanol (0-10%) gradient. The combined pure fractions were reduced in vacuo to yield the title compound as a yellow solid.

Workup

  1. customInto a round bottom flask was combined
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 2 hours
  4. temperatureto cool
  5. customthe volatiles were removed under reduced pressure
  6. customThe crude oil was chromatographed

Sources & evidence

ORD record
ord-2e2bcda050574e819a62e430ec70528c
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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