Triethylamine → 1158756-43-4

HRID 2167438Notes

Reaction equation

HRID 2167438 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:18]O)=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[Br:27]P(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([CH2:18][Br:27])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24614Phosphorus tribromideHCID 516892Sodium BicarbonateHCID 58398107HCID 58398107, compound

Product 1

HCID 669783501158756-43-4Yield 61.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.380 mmol of tert-butyl-7-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate in 2.5 ml CH2Cl2 were added at 0° C. 1.139 mmol Et3N and 0.456 mmol tribromophosphine. The mixture was allowed to warm to room temperature and stirred for 1 h. To the reaction mixture were added saturated NaHCO3 solution and EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layers were washed, dried over MgSO4 and filtered. Evaporation of the solvent gave 105 mg of crude material that was purified by flash chromatography to yield 76 mg of colorless oil (61.3%).

Workup

  1. extractionThe aqueous layer was extracted with EtOAc
  2. washThe combined organic layers were washed
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customEvaporation of the solvent
  6. customgave 105 mg of crude material that
  7. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-81052eac9bb44ac0a34ca43873628cdb
Source dataset
uspto-grants-2015_06
Patent number
US09045459B2

Reaction notes

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