Sodium borohydride → HCID 59408994, compound

HRID 1894723Notes

Reaction equation

HRID 1894723 reaction equation
[C:1]1([C:13](=O)[CH2:14][C:15]#[N:16])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1.[BH4-].[Na+]>CN(C)C=O>[C:1]1(/[CH:13]=[CH:14]/[C:15]#[N:16])[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59408992HCID 59408992, compound

Product 1

HCID 59408994HCID 59408994, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a room temperature stirred solution of 3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-3-oxo-propionitrile (1.0 g, 4.5 mmol) in anhydrous N,N-dimethylformamide (20 ml) was added excess sodium borohydride in small portions over 3 days. After 5 days the mixture was quenched with 1M hydrochloric acid (50 ml) and extracted with ethyl acetate (3×100 ml). The organic layer was dried over anhydrous magnesium sulfate and evaporated to dryness. The residue obtained was purified by flash column chromatography (SiO2, 20% EtOAc in hexanes) to afford (E)-3-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-acrylonitrile as an off white solid (348 mg). 400 MHz 1H NMR (CDCl3) δ: 7.55 (d, J=8.0 Hz, 1H), 7.5 (d, J=16.4 Hz, 1H), 7.3 (s, 1H), 7.18 (t, J=7.6 Hz, 1H), 7.03 (dd, J=0.8 and 6.8 Hz, 1H), 5.7 (d, J=16.4 Hz, 1H), 4.17 (t, J=5.6 Hz, 2H), 3.0 (t, J=6.4 Hz, 2H), 2.28-2.22 (m, 2H); LCMS: 208 [M+].

Workup

  1. customAfter 5 days the mixture was quenched with 1M hydrochloric acid (50 ml)
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue obtained
  6. customwas purified by flash column chromatography (SiO2, 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5a5b46dcb7fe4f0ead2ea5838f8f853d
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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