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

HRID 1747039Notes

Reaction equation

HRID 1747039 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]=[N+]=[N-])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O>[C:1]([O:5][C:6](=[O:19])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][NH2:16])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 59478385t-Butyl [3-(azidomethyl)phenoxy]acetate

Product 1

HCID 20758042t-Butyl [3-(aminomethyl)phenoxy]acetateYield 88.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixed liquid of 5.16 g of t-butyl[3-(azidomethyl)phenoxy]acetate and 50 ml of THF were added 6.17 g of triphenylphosphine and 1.04 ml of water, followed by stirring at room temperature for 4 days. The solvent was evaporated and diisopropyl ether was added thereto. The precipitated solid was separated by filtration and the solvent was evaporated again. The residue was purified by silica gel column chromatography (eluent:chloroform-methanol-saturated aqueous ammonia) to obtain 4.10 g of t-butyl[3-(aminomethyl)phenoxy]acetate as a pale yellow oily substance.

Workup

  1. customThe solvent was evaporated
  2. additiondiisopropyl ether was added
  3. customThe precipitated solid was separated by filtration
  4. customthe solvent was evaporated again
  5. customThe residue was purified by silica gel column chromatography (eluent:chloroform-methanol-saturated aqueous ammonia)

Sources & evidence

ORD record
ord-74ad680519c541c289ec9e9a5a73017f
Source dataset
uspto-grants-2015_10
Patent number
US09150541B2

Reaction notes

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