Benzaldehyde → (+/-)-trans-2-Benzyl-6-(trifluoromethyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-one

HRID 2100637Notes

Reaction equation

HRID 2100637 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[C:12]2[C:11](=[O:13])[NH:10][C@@H:9]3[CH2:14][NH:15][CH2:16][C@H:8]3[C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH:19]([C:21]1[CH:30]=[CH:29][CH:28]=[C:27](C(F)(F)F)[C:22]=1C(OC)=O)=O.C(=O)C1C=CC=CC=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C.C([O-])(O)=O.[Na+]>[CH2:19]([N:15]1[CH2:16][C@@H:8]2[C@H:9]([NH:10][C:11](=[O:13])[C:12]3[C:3]([C:2]([F:1])([F:17])[F:18])=[CH:4][CH:5]=[CH:6][C:7]=32)[CH2:14]1)[C:21]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:22]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 57799321(+/-)-trans-6-(trifluoromethyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-oneHCID 86090086HCID 86090086, compound

Product 1

HCID 69052117(+/-)-trans-2-Benzyl-6-(trifluoromethyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-oneYield 83%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (±)-trans-6-(trifluoromethyl)-2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-one, the free base of Example 10, (161 mg, 0.63 mmol) in 4 mL of 1,2-dichloroethane was added benzaldehyde (0.076 mL, 0.76 mmol), sodium triacetoxyborohydride (267 mg, 1.26 mmol) and 3 drops of glacial acetic acid. The mixture was allowed to stir at ambient temperature for 3 h. The reaction was diluted with sat'd aq NaHCO3 and extracted with ethyl acetate. The organics were washed with brine, dried (MgSO4) and concentrated in vacuo to afford 180 mg (83%) of the title compound which was sufficiently pure to be used without purification. LRMS (ESI): 347.2 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cfe58908f26341408f1fff073f2291b6
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

Loading…