Acetic Acid → HCID 14182871, compound

HRID 1638987Notes

Reaction equation

HRID 1638987 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[C:11](=[O:18])[C:10]3([CH2:22][CH2:21][CH2:20][CH2:19]3)[C:9]2=[O:23])[CH:5]=[CH:6][CH:7]=1.CCO.[BH3-]C#N.[Na+].C(O)(=O)C>C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][N:16]=3)[CH:11]([OH:18])[C:10]3([CH2:22][CH2:21][CH2:20][CH2:19]3)[C:9]2=[O:23])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 702EthanolHCID 5003444Sodium cyanoborohydride2×HCID 13823464HCID 13823464, compound

Product 1

HCID 14182871HCID 14182871, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.2 g (6.73 mmol.) of 1'-(3-chlorophenyl)-spiro[cyclopentane-1,3'-[1,8]-naphthyridin]-2',4'-(1'H)dione in 176 mL of (1:1) THF: EtOH (abs.) was added 2.54 g (40 mmol.) of NaBH3CN and 3.0 mL of acetic acid. The solution was stirred at room temperature. An additional 0.2 g (3.2 mmol.) of NaBH3CN and 0.3 mL of acetic acid were added on the fourth day. After 9 days the reaction was stopped by slow addition of 10 mL of water. After concentration, the residue was purified by column chromatography, eluting with CHCl3 -CH3OH(95:5) to yield a colorless solid, 1.82 g. (5.53 mmol. 82%).

Workup

  1. concentrationAfter concentration
  2. customthe residue was purified by column chromatography
  3. washeluting with CHCl3 -CH3OH(95:5)
  4. customto yield a colorless solid, 1.82 g

Sources & evidence

ORD record
ord-0ddf35819c0e4a60a6146b2931c6b5c0
Source dataset
uspto-grants-1989_11
Patent number
US04882332

Reaction notes

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