Methanol → HCID 59515907, compound

HRID 1161215Notes

Reaction equation

HRID 1161215 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][CH:17]1[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]1.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][CH:17]1[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]1)[C:9]2=[O:14])([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 100127605-nitro-1H-isochromen-1-oneHCID 10679125Tert-butyl 3-(aminomethyl)azetidine-1-carboxylate

Product 1

HCID 59515907HCID 59515907, compound

Procedure

Into a round bottom flask was combined 5-nitro-isochromen-1-one (0.5 g, 0.002 mol), tert-butyl 3-(aminomethyl)azetidine-1-carboxylate (0.975 g, 0.00523 mol), methanol (15 mL, 0.37 mol), and the mixture was heated at reflux for 2 hours. The mixture was cooled to room temperature. LC-MS showed that the starting material was completely consumed. Volatiles were removed and the resulting oil was purified by silica-gel twice in a methanol:methylene chloride (0-10%) gradient and in a EtoAc:Hexane(30-80%). A light yellow solid was obtained (0.56 g). m/z=360.0 (M+1).

Workup

  1. customInto a round bottom flask was combined
  2. temperatureat reflux for 2 hours
  3. customwas completely consumed
  4. customVolatiles were removed
  5. customthe resulting oil was purified by silica-gel twice in a methanol
  6. customA light yellow solid was obtained (0.56 g)

Sources & evidence

ORD record
ord-74bc5b1fd559482c8f030d4b7193f268
Source dataset
uspto-grants-2010_10
Patent number
US07816371B2

Reaction notes

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