Sodium borohydride → HCID 118208785, compound

HRID 595192Notes

Reaction equation

HRID 595192 reaction equation
[C:1]([CH:4]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[O:18][CH3:19])[C:6](=[O:20])[CH2:5]1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO.O>[CH3:19][O:18][C:11]1[CH:12]=[C:13]([O:16][CH3:17])[CH:14]=[CH:15][C:10]=1[CH2:9][N:7]1[CH2:8][CH:4]([CH:1]([OH:3])[CH3:2])[CH2:5][C:6]1=[O:20]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 118208857HCID 118208857, compound

Product 1

HCID 118208785HCID 118208785, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-acetyl-1-(2,4-dimethoxybenzyl)pyrrolidin-2-one (1.5 g, 7.2 mmol) in MeOH (15 mL), NaBH4 (400 mg, 10.8 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 1 hour then diluted with water and extracted with EtOAc. The organic layers were dried over sodium sulfate and concentrated under reduced pressure to afford 1-(2,4-dimethoxybenzyl)-4-(1-hydroxyethyl)pyrrolidin-2-one. 1H NMR (400 MHz, CDCl3) δ 7.10-7.13 (m, 1H), 6.43-6.45 (m, 2H), 4.41-4.42 (m, 2H), 3.79-3.82 (m, 6H), 3.67-3.70 (m, 1H), 3.06-3.46 (m, 2H), 2.03-2.50 (m, 3H), 1.26-1.42 (d, J=7.2 Hz, 3H). MS ESI calc'd. for C15H22NO4 [M+H]+ 280. found 280.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layers were dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ab8e2963ae97489491944c7687c24286
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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