Methanol → HCID 86640052, compound

HRID 2427260Notes

Reaction equation

HRID 2427260 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:9]2[NH:8][C:7]3[CH2:12][CH:13]([NH:15][C:16](=[O:20])[CH:17]([CH3:19])[CH3:18])[CH2:14][C:6]=3[C:5]=2[CH:4]=1)#[N:2].[OH-:21].[Na+].[CH3:23]O>O>[CH3:23][O:21][N:2]=[CH:1][C:3]1[CH:11]=[CH:10][C:9]2[NH:8][C:7]3[CH2:12][CH:13]([NH:15][C:16](=[O:20])[CH:17]([CH3:18])[CH3:19])[CH2:14][C:6]=3[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67252702HCID 67252702, compound

Product 1

HCID 86640052HCID 86640052, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Mix (±)-N-[7-cyano-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl]-isobutyramide (5 g, 18.7 mmol) and Al—Ni catalyst (15 g) in water/96% formic acid, 1/10 (110 mL). Reflux for 18 h, add Al—Ni catalyst (13 g) and reflux another 5 h. Cool and dilute with MeOH and filter off the inorganics. Concentrate the filtrate, add EtOH (200 mL) and sonicate for 15 min. Filter insoluble material and to the crude aldehyde solution add O-methoxyamine-HCl (120 mmol) dissolved in water (25 mL) and make the mixture basic (pH=9-12) with 5.0 N NaOH. Stir at room temperature for 18 h and remove most of the solvent under reduced pressure. Mix the residue with water and sonicate for 30 min. Isolate 4.39 g of a brown solid. Purify the material on silica gel using 30-100% EtOAc/hexane to give 530 mg (10%) title compound as a pale yellow solid. MS (m/z): 300 (M+1), 298 (M−1).

Workup

  1. temperatureReflux for 18 h
  2. temperaturereflux another 5 h
  3. temperatureCool
  4. filtrationfilter off the inorganics
  5. concentrationConcentrate the filtrate
  6. additionadd EtOH (200 mL)
  7. customsonicate for 15 min
  8. customremove most of the solvent under reduced pressure
  9. additionMix the residue with water
  10. customsonicate for 30 min

Sources & evidence

ORD record
ord-1e8248b3109d49998d1025970e05dc0b
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

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