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

HRID 2077061Notes

Reaction equation

HRID 2077061 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 0.1N 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 0.1N HCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4c55adc19b644adbabd07ee2c39c6526
Source dataset
uspto-grants-2011_04
Patent number
US07928109B2

Reaction notes

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