Borane → HCID 18470864, compound

HRID 2228744Notes

Reaction equation

HRID 2228744 reaction equation
B.[C:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[C:8]([NH:10][CH2:11]OC)=[O:9])#[N:3].[O:17]1[CH2:21]CC[CH2:18]1>>[NH2:3][CH2:2][CH2:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][CH:16]=1)[C:8]([NH:10][CH2:11][CH2:18][O:17][CH3:21])=[O:9]

Participants

4

Reactant 3

HCID 6331BoraneHCID 8028TetrahydrofuranHCID 18470906HCID 18470906, compound

Product 1

HCID 18470864HCID 18470864, compound

Procedure

Borane (1N in tetrahydrofuran, 467 ml, 0.467 mol) was added dropwise to a solution of 3-(cyanomethyl)N-(methoxymethyl)benzamide (14.57 g, 0.067 mol) [see preparation 40] in tetrahydrofuran (30 ml) over 20 minutes. The reaction mixture was then stirred at room temperature for 18 hrs and then heated to reflux for 2 hrs, after which time the solvent was evaporated under reduced pressure and the residue acidified with hydrochloric acid (2N). The resultant mixture was heated to reflux for 10 minutes after which time it was basified with sodium hydroxide. The product was extracted with dichloromethane (3×30 ml), the combined organic layers were dried over MgSO4 and the solvent evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol:0.88 ammonia (95:5:0.5) changing to (92.5:7.5:0.25) changing to (90:10:1) to afford the title compound, 6.15 g, (44%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hrs
  3. customafter which time the solvent was evaporated under reduced pressure
  4. temperatureThe resultant mixture was heated
  5. temperatureto reflux for 10 minutes after which time it
  6. extractionThe product was extracted with dichloromethane (3×30 ml)
  7. dry with materialthe combined organic layers were dried over MgSO4
  8. customthe solvent evaporated under reduced pressure
  9. customThe crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane

Sources & evidence

ORD record
ord-d80cc4802f204a7d84d0ab731a633082
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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