Benzyl Alcohol → (2-Benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)carbamic acid benzyl ester

HRID 750230Notes

Reaction equation

HRID 750230 reaction equation
[CH2:1]([N:8]1[C:17](C(O)=O)=[C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Br:27])[CH:14]=2)[C:9]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:31]([CH2:34]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:43])C=CC=CC=1.[CH2:53]([OH:60])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>C1(C)C=CC=CC=1>[CH2:53]([O:60][C:34](=[O:43])[NH:31][C:17]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9](=[O:28])[C:10]2[C:15]([C:16]=1[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[CH:14][C:13]([Br:27])=[CH:12][CH:11]=2)[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 230606482-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid

Product 1

HCID 69157122(2-Benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)carbamic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 2-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid (300 mg), triethylamine (98 μl) and toluene (6.0 ml) was added diphenylphosphorylazide (257 μl) at room temperature with stirring, and the mixture was stirred at room temperature for 1 hr. and at 80° C. for 1 hr. After cooling the reaction mixture, benzyl alcohol (86 μl) was added, and the mixture was further stirred at 80° C. for 12 hrs. After cooling the reaction mixture, the solvent was evaporated and the residue was purified by medium pressure preparative LC (hexane/ethyl acetate=9/1-1/1) to give (2-benzyl-6-bromo-1-oxo-4-phenyl-1,2-dihydroisoquinolin-3-yl)carbamic acid benzyl ester as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. additionwas added
  3. stirringthe mixture was further stirred at 80° C. for 12 hrs
  4. temperatureAfter cooling the reaction mixture
  5. customthe solvent was evaporated
  6. customthe residue was purified by medium pressure preparative LC (hexane/ethyl acetate=9/1-1/1)

Sources & evidence

ORD record
ord-b6657fa15ece4a54ad1a281dc0df88bc
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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