Sodium Bicarbonate → (R)-tert-butyl 1-(4-nitrophenyl)ethylcarbamate

HRID 886989Notes

Reaction equation

HRID 886989 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([C@H:11]([NH2:13])[CH3:12])=[CH:7][CH:6]=1)([O-:4])=[O:3].[C:14](=[O:17])(O)[O-:15].[Na+]>C(Cl)Cl>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([C@H:11]([NH:13][C:14](=[O:17])[O:15][C:8]([CH3:11])([CH3:9])[CH3:7])[CH3:12])=[CH:9][CH:10]=1)([O-:4])=[O:3]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 16212177(R)-alpha-Methyl-4-nitrobenzylamine hydrochloride

Product 1

HCID 57584601(R)-tert-butyl 1-(4-nitrophenyl)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

(R)-1-(4-nitrophenyl)ethanamine hydrochloride salt (1.0 g, 4.9 mmol), tert-butoxycarbonyl (BOC) anhydride (1.18 g, 5.43 mmol), and 10.0 mL of 1M sodium bicarbonate solution were dissolved in DCM (15 mL) and allowed to stir at 25° C. for 24 h. The organic layer was collected, and the aqueous layer was washed with DCM. The combined organic layers were then washed with water and 0.1 N HCl, dried over MgSO4, filtered, and concentrated to provide C1 as a white solid. Yield: 1.2 g, 92%. GC-MS=266. 1H NMR (500 MHz, d6-DMSO) δ: 8.15 (d, 2H), 7.56 (d, 1H), 7.52 (d, 2H), 4.68 (m, 1H), 1.32 (s, 9H), 1.27 (d, 3H).

Workup

  1. customThe organic layer was collected
  2. washthe aqueous layer was washed with DCM
  3. washThe combined organic layers were then washed with water and 0.1 N HCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ee887c16d06a4c9b91d00b916cf80b9e
Source dataset
uspto-grants-2012_08
Patent number
US08247411B2

Reaction notes

Loading…