Hydrochloric Acid → tert-Butyl 2-(4-bromophenyl)propan-2-ylcarbamate

HRID 1628093Notes

Reaction equation

HRID 1628093 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH2:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.Cl.[O:13](C(OC(C)(C)C)=O)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:11][C:14](=[O:13])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:9])[CH3:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 90495Di-tert-butyl dicarbonateHCID 230091162-(4-Bromophenyl)propan-2-amine

Product 1

HCID 18183247tert-Butyl 2-(4-bromophenyl)propan-2-ylcarbamateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(4-bromophenyl)propan-2-amine, hydrochloric acid (1.0 g, 4.0 mmol, AKOS) in DCM (30 mL) at about 0° C. was added TEA (1.11 mL, 7.98 mmol). A solution of BOC2O (1.623 ml, 7.01 mmol) in DCM (10 mL) was added dropwise over about 10 min. After about 30 min, the ice bath was removed and the mixture was stirred overnight at rt. The mixture was diluted with water (30 mL) and extracted with DCM (2×30 mL). The organic layers were combined, dried over MgSO4, filtered, and concentrated in vacuo. The crude material was purified by flash chromatograph (40 g silica gel column, 0-40% EtOAc/Heptane) to give tert-butyl 2-(4-bromophenyl)propan-2-ylcarbamate the title compound (1.13 g, 90%): LC/MS (Table 2, Method b) Rt=2.66 min.; MS m/z: 315 (M+H)+.

Workup

  1. customthe ice bath was removed
  2. additionThe mixture was diluted with water (30 mL)
  3. extractionextracted with DCM (2×30 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatograph (40 g silica gel column, 0-40% EtOAc/Heptane)

Sources & evidence

ORD record
ord-1abffbde526149fd9a2edd6bbb6a19a5
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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