Water → HCID 59139448, compound

HRID 599853Notes

Reaction equation

HRID 599853 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:5]([O:29][C:30](=[O:34])[N:31]([CH3:33])[CH3:32])=[CH:6][C:7]2[O:12][C:11](=[O:13])[C:10]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=3)=[C:9]([CH2:24][C:25](=[O:27])[CH3:26])[C:8]=2[CH:28]=1.O>C1COCC1>[Cl:3][C:4]1[C:5]([O:29][C:30](=[O:34])[N:31]([CH3:33])[CH3:32])=[CH:6][C:7]2[O:12][C:11](=[O:13])[C:10]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=3)=[C:9]([CH2:24][CH:25]([OH:27])[CH3:26])[C:8]=2[CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 59139370HCID 59139370, compound

Product 1

HCID 59139448HCID 59139448, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (49 mg, 1.30 mmol) was added to a solution of dimethylcarbamic acid 6-chloro-3-(3-nitrobenzyl)-2-oxo-4-(2-oxopropyl)-2H-1-benzopyran-7-yl ester (compound 7f-1-3CO) (300 mg, 0.65 mmol) in anhydrous THF (5.0 mL), and the mixture was stirred at 0° C. for 2 hours. The reaction mixture was then poured into water and extracted with ethyl acetate. The organic extract was washed with saturated saline and dried over magnesium sulfate, and the title compound (280 mg, 93%) was obtained as a pale yellow powder.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with saturated saline
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-417560712104437889734991ebaa2f39
Source dataset
uspto-grants-2011_03
Patent number
US07897792B2

Reaction notes

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