Potassium Phosphate, Tribasic → HCID 68670682, compound

HRID 2070965Notes

Reaction equation

HRID 2070965 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10].[CH:17]1(B(O)O)[CH2:19][CH2:18]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:17]1([C:2]2[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=2)[CH2:5][NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:19][CH2:18]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 11033439tert-Butyl 3-bromobenzylcarbamate

Product 1

HCID 68670682HCID 68670682, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl 3-bromobenzylcarbamate (572 mg, 2 mmol), cyclopropyl boronic acid (223 mg, 2.6 mmol), potassium phosphate (1.49 g, 7.0 mmol) and tricyclohexyl phosphine (56 mg, 0.2 mmol) in toluene (9 mL) and water (0.45 mL) under a nitrogen atmosphere was added palladium acetate (22 mg, 0.1 mmol). The mixture was heated at 100° C. for 3 h and then cooled to rt. Water (20 mL) was added and the mixture extracted with EtOAc (2×30 mL), the combined organic extracts were washed with brine (20 mL), dried over Na2SO4 and concentrated in vacuo. Crude product was purified by column chromatography (15% EtOAc in hexanes) afforded tert-butyl 3-cyclopropylbenzylcarbamate as a colorless oil in 93% yield. (3-cyclopropylphenyl)methanamine was then generated by removing the Boc protecting group by treatment with HCl (in methanol or dioxane) or trifluoroacetic acid in dichloromethane.

Workup

  1. temperaturecooled to rt
  2. extractionthe mixture extracted with EtOAc (2×30 mL)
  3. washthe combined organic extracts were washed with brine (20 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customCrude product was purified by column chromatography (15% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7757fb4885b948e4bff1126410942a45
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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