Benzyl Chloroformate

Used Chemicals

• Benzyl Chloroformate (= Cbz-Cl) [B3021]
• Benzylamine [B0406]
• Triethylamine (= Et₃N) [T0424]
• Dichloromethane

Procedure

Benzyl carbonochloridate (1.69 mL, 12 mmol) was added dropwise with a syringe to a solution of triethylamine (2.8 mL, 20 mmol) and benzylamine (1.1 mL, 10 mmol) in dichloromethane (20 mL), cooling with ice/water and stirred at room temperature for 24 hours. The reaction mixture was washed with water (20 mL) and the aqueous layer was extracted with dichloromethane (10 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to afford N-(benzyloxycarbonyl)benzylamine (1.98 g, 82% yield) as a white solid.

Experimenter’s Comments

The reaction solution was monitored by UPLC.
The solvent was dehydrated with MS4A before use.

Analytical Data

N-(Benzyloxycarbonyl)benzylamine

¹H NMR (400 MHz, DMSO-d₆); δ 7.37-7.28 (m, 10H), 5.13 (s, 2H), 5.09 (s, 1H), 4.40 (d, J = 6.0 Hz, 2H).

Other References

• Diborylmethyl Group as a Transformable Building Block for the Diversification of Nitrogen-Containing Molecules
• C. Hwang, Y. Lee, M. Kim, Y. Seo, S. H. Cho, Angew. Chem. Int. Ed. 2022, 61, e202209079.

Reference

• V. Perron, S. Abbott, N. Moreau, D. Lee, C. Penney, B. Zacharie, Synthesis 2009, 283.