Sodium borohydride → HCID 59165958, compound

HRID 1442810Notes

Reaction equation

HRID 1442810 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:13][CH2:14][N+:15]([O-])=O)[C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>CO>[NH2:15][CH2:14][CH2:13][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59166099HCID 59166099, compound

Product 1

HCID 59165958HCID 59165958, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-(3-bromophenyl)-4-nitrobutanoate (3.1 g, 11 mmol) and NiCl2-6 H2O (5.4 g, 23 mmol) in methanol (12 mL) was added NaBH4 (1.3 g, 34 mmol). The reaction mixture was stirred for 1 minute and was quenched by adding ice water. The mixture was filtered, and the filtrate was extracted with ethyl acetate (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under the reduced pressure to give methyl 4-amino-2-(3-bromophenyl)-butanoate (2.5 g, 82%) as a white solid, which was directly used in the next step without further purification.

Workup

  1. customwas quenched
  2. additionby adding ice water
  3. filtrationThe mixture was filtered
  4. extractionthe filtrate was extracted with ethyl acetate (50 mL×3)
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under the reduced pressure

Sources & evidence

ORD record
ord-f20c4ffd97ce406faea1334abcafdfb1
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

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