Potassium Carbonate → Tert-butyl(trans)-2-(4-(3-bromobenzyloxy)phenyl)cyclopropylcarbamate

HRID 1023822Notes

Reaction equation

HRID 1023822 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][C@@H:8]1[CH2:10][C@H:9]1[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Br:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29]Br>CN(C=O)C>[Br:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH2:29][O:17][C:14]1[CH:15]=[CH:16][C:11]([C@@H:9]2[CH2:10][C@H:8]2[NH:7][C:6](=[O:18])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 699793-Bromobenzyl bromideHCID 86672576tert-Butyl N-[(1R,2S)-rel-2-(4-hydroxyphenyl)cyclopropyl]carbamate2×

Product 1

HCID 86680873Tert-butyl(trans)-2-(4-(3-bromobenzyloxy)phenyl)cyclopropylcarbamateYield 62.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl-(trans)-2-(4-hydroxyphenyl)cyclopropylcarbamate (Intermediate N, 5 g, 20.0 mmol), K2CO3 (6.8 g, 50.0 mmol) in dry DMF (10 vols) was added 3-Bromo benzyl bromide (5 g, 20.0 mmol) and stirred at RT for 16 h. After completion, the reaction mixture was poured into ice water (150 mL) and extracted with EtOAc (2×75 mL). The combined extracts were washed with water (100 mL), brine (100 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by flash chromatography to give (tert-butyl (trans)-2-(4-(3-bromobenzyloxy)phenyl)cyclopropylcarbamate (5.2 g, 62%) as a white solid. The crude was carried to next step without further purification.

Workup

  1. extractionextracted with EtOAc (2×75 mL)
  2. washThe combined extracts were washed with water (100 mL), brine (100 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-f23a107933e84c34ab1aa3df13e99a0f
Source dataset
uspto-grants-2014_05
Patent number
US08722743B2

Reaction notes

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