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

HRID 450762Notes

Reaction equation

HRID 450762 reaction equation
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH:17]=[CH:18][CH:19]=1)[O:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[N+]=[N-].C1COCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O>[C:13]([O:12][C:10](=[O:11])[CH2:9][O:8][C:7]1[CH:17]=[CH:18][CH:19]=[C:5]([CH2:4][NH2:1])[CH:6]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 59478385HCID 59478385, compound

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-45a75f2dbaf74dce9d4e3479707941e5
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Reaction notes

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