ChemicalBook CAS DataBase List Cbz-D-Phenylalaninol

Cbz-D-Phenylalaninol synthesis

7synthesis methods

Product Name:Cbz-D-Phenylalaninol
CAS Number:58917-85-4
Molecular formula:C17H19NO3
Molecular Weight:285.34

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1885-14-9 Synthesis

1885-14-9
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Yield: 73%

Reaction Conditions:

with triethylamine in dichloromethane

Steps:

19.a
To a methylene chloride solution (80 mL) of D-phenylalaninol 18a (1.15 g, 7.61 mmol) was added triethylamine (1.59 mL, 11.4 mmol) and benzyl chloroformate (1.19 mL, 8.37 mmol). The mixture was stirred for 3 h and then concentrated. The residue was dissolved in methylene chloride (50 mL) and washed with brine (1×50 mL). The solution was dried (Na₂SO₄) and concentrated. After column chromatography purification (10 to 30% EtOAc in hexanes), the compound 19a was obtained in 73% yield (1.59 g). ¹H NMR (CDCl₃): δ 7.46-7.15 (10H, m), 5.11 (2H, s), 4.96 (1H, m), 3.98 (1H, m), 3.72 (1H, m), 3.63 (1H, m), 2.89 (1H, d, J=7.2 Hz); MS (ESP): 286 (M+H⁺); 284 (M-H)^-.

References:

Pfizer Inc. US2005/250742, 2005, A1 Location in patent:Page/Page column 31

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