Acetic Acid → HCID 11952000, compound

HRID 1669073Notes

Reaction equation

HRID 1669073 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[O-:6][N+:7]1[C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][C:11]=2[N:10]=[C:9]([CH2:20][CH2:21][CH:22]=O)[N:8]=1)[CH2:17][CH2:16][CH2:15]3.[BH3-]C#N.[Na+].CC(O)=O>CO>[N:1]1([CH2:22][CH2:21][CH2:20][C:9]2[N:8]=[N+:7]([O-:6])[C:12]3[CH:13]=[C:14]4[C:18]([CH2:17][CH2:16][CH2:15]4)=[CH:19][C:11]=3[N:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5003444Sodium cyanoborohydrideHCID 57786560HCID 57786560, compound

Product 1

HCID 11952000HCID 11952000, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyrrolidine (3.0 g, 42 mmol) was added to a stirred solution of propanal 75 (1.5 g, 6.2 mmol) in MeOH (100 mL) at 0° C. and the solution stirred for 30 min. NaCNBH3 (1.5 g, 24 mmol) was added and the solution stirred at 0° C. for 30 min and then HOAc (2 mL) was added and the mixture was stirred at 20° C. for 16 h. The solvent was evaporated and the residue was partitioned between DCM (200 mL) and water (200 mL). The aqueous phase was extracted with DCM (2×200 mL), the combined organic phase was dried and the solvent evaporated. The residue was purified by chromatography, eluting with 10% MeOH/EtOAc, to give 1-oxide 84 (1.5 g, 84%) as a yellow oil: 1H NMR [(CD3)2SO] δ 8.25 (s, 1H, H-9), 7.74 (s, 1H, H-5), 3.10-3.16 (m, 4H, H-6, H-8), 3.02-3.09 (m, 2H, CH2N), 2.80-2.88 (m, 6H, 3×CH2), 2.17-2.28 (m, 4H, H-7, CH2), 1.82-1.90 (m, 4H, 2×CH2); 13C NMR δ 165.0, 154.8, 149.2, 147.2, 132.3, 122.7, 114.3, 55.0, 53.4 (2), 34.8, 33.2, 32.8, 25.7, 25.5, 23.4 (2); HRMS calcd for C17H22N4O (M+) m/z 298.1794, found 298.1794.

Workup

  1. stirringthe solution stirred at 0° C. for 30 min
  2. stirringthe mixture was stirred at 20° C. for 16 h
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between DCM (200 mL) and water (200 mL)
  5. extractionThe aqueous phase was extracted with DCM (2×200 mL)
  6. customthe combined organic phase was dried
  7. customthe solvent evaporated
  8. customThe residue was purified by chromatography
  9. washeluting with 10% MeOH/EtOAc

Sources & evidence

ORD record
ord-41e640eea8684837844f23ccab948ee9
Source dataset
uspto-grants-2011_08
Patent number
US07989451B2

Reaction notes

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