Water → HCID 59395014, compound

HRID 1465098Notes

Reaction equation

HRID 1465098 reaction equation
[CH:1]1([C:6]2[C:7]([OH:20])=[CH:8][C:9]([N+:17]([O-])=O)=[C:10]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.O>C(O)(=O)C.CO.[Zn]>[NH2:17][C:9]1[CH:8]=[C:7]([OH:20])[C:6]([CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:11][C:10]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14]

Participants

6

Reactant 2

HCID 962WaterHCID 59395065HCID 59395065, compound

Product 1

HCID 59395014HCID 59395014, compoundYield 93.4%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Methyl 2-(5-cyclopentyl-4-hydroxy-2-nitro-phenyl)acetate (30 mg, 0.11° mmol) was dissolved in acetic acid (1 mL) and water (0.5 mL) and treated with Zn dust (7 mg, 0.98 μL, 0.11 mmol) at room temperature. The mixture was stirred for 2 h then diluted with methanol (5 mL) and filtered. The filtrate was diluted with ethyl acetate, washed with 50% saturated NaHCO3 (2×20 mL), water, and brine. The solution was dried over Na2SO4, filtered, and dried down to provide methyl 2-(2-amino-5-cyclopentyl-4-hydroxyphenyl)acetate as an amber colored oil (25 mg, 93% yield). LC/MS m/z 249.8 [M+H]+.

Workup

  1. filtrationfiltered
  2. additionThe filtrate was diluted with ethyl acetate
  3. washwashed with 50% saturated NaHCO3 (2×20 mL), water, and brine
  4. dry with materialThe solution was dried over Na2SO4
  5. filtrationfiltered
  6. customdried down

Sources & evidence

ORD record
ord-e240b820bdcb481da9499474ac99397f
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

Loading…