Sodium Azide → tert-Butyl [1-(4-bromophenyl)cyclobutyl]carbamate

HRID 2104129Notes

Reaction equation

HRID 2104129 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(C(O)=O)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:15][C:16]([O:19][C:20]([O:22]C(OC(C)(C)C)=O)=O)([CH3:18])[CH3:17].[N-:30]=[N+]=[N-].[Na+].C(=O)(O)[O-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.FC(F)(F)S([O-])(=O)=O.[Zn+2].FC(F)(F)S([O-])(=O)=O.CCOC(C)=O>[C:16]([O:19][C:20](=[O:22])[NH:30][C:8]1([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:18])([CH3:17])[CH3:15]

Participants

9

Reactant 4

HCID 33557Sodium AzideHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 167699191-(4-Bromophenyl)cyclobutane-1-carboxylic acid

Product 1

HCID 52988051tert-Butyl [1-(4-bromophenyl)cyclobutyl]carbamate

Reagents, catalysts & solvents 4

HCID 74236Tetrabutylammonium BromideCatalystHCID 104671Zinc trifluoromethanesulfonateCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(4-bromophenyl)cyclobutanecarboxylic acid (7-1, 10.89 g, 42.7 mmol), Boc anhydride (10.90 mL, 47.0 mmol), sodium azide (9.71 g, 149 mmol), tetrabutylammonium bromide (2.048 mL, 6.40 mmol) and zinc trifluoromethansulfonate (0.155 g, 0.427 mmol) were stirred in THF (100 ml) at 60° for 4 h. The reaction mixture was cooled to room temperature and EtOAc and saturated aqueous sodium bicarbonate were added to the mixture. The suspension was filtered through a glass frit and the filtrate was extracted with EtOAc, washing with water and brine. The organic layer was dried over Na2SO4, filtered and reduced in vacuo to a tan oil. The crude product was purified by normal phase flash chromatography eluting with 5-15% EtOAc/Hex to give 7-2 as a white solid.

Workup

  1. filtrationThe suspension was filtered through a glass frit
  2. extractionthe filtrate was extracted with EtOAc
  3. washwashing with water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customThe crude product was purified by normal phase flash chromatography
  7. washeluting with 5-15% EtOAc/Hex

Sources & evidence

ORD record
ord-b8c2819607184ac69034d983164d0dee
Source dataset
uspto-grants-2009_08
Patent number
US07576209B2

Reaction notes

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