Pyridine → t-Butyl [3-(aminomethyl)phenoxy]acetate

HRID 2300569Notes

Reaction equation

HRID 2300569 reaction equation
C(OC(=O)C)(C)(C)C.[C:9]([O:13][C:14](=[O:25])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=O)[CH:18]=1)([CH3:12])([CH3:11])[CH3:10].NO.Cl.[N:29]1C=CC=CC=1>CO>[C:9]([O:13][C:14](=[O:25])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][NH2:29])[CH:18]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 1049PyridineHCID 10908tert-Butyl acetateHCID 443297Hydroxyamine hydrochlorideHCID 14971816tert-Butyl (3-formylphenoxy)acetate

Product 1

HCID 20758042t-Butyl [3-(aminomethyl)phenoxy]acetate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(3-Hydroxyimino-methyl)-phenoxy)-acetic acid tert-butyl ester. To a solution of (3-formyl-phenoxy)-acetic acid tert-butyl ester prepared of Preparation 20, Step A (2.05 g, 8.68 mmol) in MeOH (30 mL) was added NH2OH.HCl (0.66 g, 9.54 mmol) and pyridine (3.5 mL, 43.4 mmol) and the reaction was stirred for 2 hours. The MeOH was removed in vacuo and the residue was diluted with EtOAc and 1N HCl. The layers were separated and the aqueous solution was washed with EtOAc. The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to afford the title compound of Step B (1.99 g). 1H NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 7.23-7.28 (m, 2H), 7.12 (m, 1H), 6.93 (d, 1H), 4.51 (s, 2H), 1.46 (s, 9H).

Workup

  1. customThe MeOH was removed in vacuo
  2. additionthe residue was diluted with EtOAc and 1N HCl
  3. customThe layers were separated
  4. washthe aqueous solution was washed with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c09fbc3fd524bea85b33dddfd16239e
Source dataset
uspto-grants-2002_12
Patent number
US06498172B1

Reaction notes

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