Sodium Carbonate → (S)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamate

HRID 1853389Notes

Reaction equation

HRID 1853389 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[O:17](C(OC(C)(C)C)=O)[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=O>C(Cl)Cl.C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:18](=[O:17])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 90495Di-tert-butyl dicarbonateHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamine

Product 1

HCID 56973617(S)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 150 g (735 mmol) (S)-1-(4-bromophenyl)ethylamine in 2 L DCM are added 459 mL (918 mmol) of an aq. Na2CO3 solution (c=2 mol/L). To this mixture a solution of 164 g (749 mmol) BOC2O in 350 mL THF is added dropwise at r.t. and stirring is continued for 1 h. Then the mixture is poured onto water and stirred for additional 20 min. The layers are separated, the org. layer is washed with water (2×), dried over Na2SO4, filtered and the solvent is removed in vacuo.

Workup

  1. additionThen the mixture is poured onto water
  2. stirringstirred for additional 20 min
  3. customThe layers are separated
  4. washlayer is washed with water (2×)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-bb92bab2862b46b79efef9f2c8fa33c9
Source dataset
uspto-grants-2015_02
Patent number
US08962641B2

Reaction notes

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