Diethyl Ether → HCID 56597423, compound

HRID 2036199Notes

Reaction equation

HRID 2036199 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]1[C:21]1[CH:26]=[C:25](Br)[CH:24]=[CH:23][C:22]=1[O:28][CH2:29][C:30]([O:32]CC)=[O:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOCC.[CH3:40][N:41](C=O)C>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]1[C:21]1[CH:26]=[C:25]([C:40]#[N:41])[CH:24]=[CH:23][C:22]=1[O:28][CH2:29][C:30]([OH:32])=[O:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 6228DimethylformamideHCID 66654234HCID 66654234, compound

Product 1

HCID 56597423HCID 56597423, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Conditions

Temperature
110 °C

Procedure

To a solution of (±)-1-(5-bromo-2-ethoxycarbonylmethoxy-phenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (105 mg, 0.20 mmol, 1.0 eq.) in DMF (10 mL) were added zinc cyanide (23 mg, 0.20 mmol, 1.0 eq.) and tetrakis(triphenylphosphine) palladium (0) (23 mg, 0.02 mmol, 0.1 eq.). The resulting suspension was stirred at 110° C. for 18 hours. After cooling, Et2O (100 mL) was added and the solution was washed with sat. aq. NaCl soln. (2×120 mL). The organic layer was dried over MgSO4, filtered, and the solvent was removed under vacuum. To a solution of the crude product in DMF (0.9 mL) 1M aq. NaOH soln. (0.25 mL) was added. The solution was stirred at r.t. for 18 hours. The solution was acidified with 1M aq. HCl soln.

Workup

  1. temperatureAfter cooling
  2. washthe solution was washed with sat. aq. NaCl soln
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent was removed under vacuum
  6. addition(0.25 mL) was added
  7. stirringThe solution was stirred at r.t. for 18 hours

Sources & evidence

ORD record
ord-e4d9413dd5144c9ba9eabdb56770c8a6
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

Loading…