Triethylamine → HCID 21835840, compound

2.29 g (11.2 mmol) of 2-(3,4-dimethylbenzyloxy)ethylazide obtained in step 2 was dissolved in 15 ml of isopropanol while stirring, and 3.1 ml (22 mmol) of triethylamine was added thereto. The mixture was added to an isopropanol solution containing 1.1 ml (11 mmol) of 1,3-propanediol and then 4.22 g (0.11 moles) of NaBH4 was added thereto. The mixture was stirred at an ambient temperature for 1 hour and the solvent was distilled off under a reduced pressure. The residue was dissolved in 10% aqueous citric acid and the resulting solution was washed three times with 30 ml of ether: hexane (1:1). The pH of the aqueous layer was adjusted to 12 with a 6N sodium hydroxide solution and then a saturated sodium chloride solution was added thereto. Thee aqueous layer was extracted with 30 ml of dichloromethane 3 times. The organic layer was dried and the solvent was evaporated under a reduced pressure to obtain 1.49 g (yield 75%) of the title compound as a colorless oil.

1. stirringThe mixture was stirred at an ambient temperature for 1 hour
2. distillationthe solvent was distilled off under a reduced pressure
3. dissolutionThe residue was dissolved in 10% aqueous citric acid
4. washthe resulting solution was washed three times with 30 ml of ether: hexane (1:1)
5. additiona saturated sodium chloride solution was added
6. extractionThee aqueous layer was extracted with 30 ml of dichloromethane 3 times
7. customThe organic layer was dried
8. customthe solvent was evaporated under a reduced pressure

ORD record

ord-07e453694b6e42079f43a77718d14af3

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05973201