Reaction #1121807

Reaction equation

(R)-tert-butyl piperidin-3-ylcarbamate

triethylamine

benzyl carbonochloridate

→

(R)-benzyl 3-(tert-butoxycarbonylamino)piperidine-1-carboxylate

Solvents

CH2Cl2

CH2Cl2

Conditions

Workup

1. 1
   Washsuccessively washed with ice cold 10% HCl (2×30 mL), water (1×30 mL), saturated NaHCO3 (1×30 mL), and brine (1×30 mL)
2. 2
   DryingThe organic phase was dried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated in vacuo
5. 5
   OtherThe residue obtained
6. 6
   Otherwas purified by flash chromatography on silica gel (Biotage Flash 60)
7. 7
   Washeluting with 20% EtOAc/hexane (3 L)
8. 8
   workup.ADDITIONThe fractions containing the product
9. 9
   Concentrationconcentrated in vacuo
10. 10
    Otherdried under high vacuum for 18 hours

Procedure

A solution of (R)-tert-butyl piperidin-3-ylcarbamate (10.00 g, 49.93 mmol) and triethylamine (20.88 mL, 149.8 mmol) in CH2Cl2 (100 mL) at 0° C. (ice bath) was treated dropwise with benzyl carbonochloridate (10.54 mL, 74.90 mmol) and stirred at 0° C. After 2 hours, the mixture was diluted with CH2Cl2 (50 mL) and successively washed with ice cold 10% HCl (2×30 mL), water (1×30 mL), saturated NaHCO3 (1×30 mL), and brine (1×30 mL). The organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The residue obtained was purified by flash chromatography on silica gel (Biotage Flash 60) eluting with 20% EtOAc/hexane (3 L). The fractions containing the product were pooled, concentrated in vacuo and dried under high vacuum for 18 hours to provide (R)-benzyl 3-(tert-butoxycarbonylamino)piperidine-1-carboxylate as a solid. LCMS (APCI+) m/z 335 (M+H)+.

Source