Water → HCID 22278940, compound

HRID 1368110Notes

Reaction equation

HRID 1368110 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:23][CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:27][C:28]1[CH:37]=[CH:36][C:31]([C:32](OC)=O)=[CH:30][CH:29]=1.[OH2:38].CN([CH:42]=[O:43])C>>[CH2:1]([O:8][C:9]([N:11]1[CH2:23][CH2:22][C:21]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:32][C:31]3[CH:30]=[CH:29][C:28]([CH2:27][C:42]([OH:43])=[O:38])=[CH:37][CH:36]=3)[C:13]=2[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 110667371,3,4,9-Tetrahydro-beta-carboline-2-carboxylic acid benzyl ester

Product 1

HCID 22278940HCID 22278940, compoundYield 93%

Procedure

To a stirred solution of 2-benzyloxycarbonyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole (5.0 g, 16.33 mmole) in dry DMF (75 mL) at 5° C. was added 60% NaH (0.98 g, 24.5 mmole). After 10 min, methyl 4-(bromomethyl)benzoate (4.12 g, 18.0 mmole) was added and the reaction was allowed to warm to RT and stir for 12 hr. The reaction contents were poured into H2O (100 mL) and extracted with EtOAc (2×100 mL). The combined organic phases were washed sequentially with H2O and brine, then were dried over Na2SO4. Concentration under reduced pressure and purification on silica (hexanes/EtOAc, 4:1) afforded the title compound (6.91 g, 93%) as a white solid: MS (ES) m/e 455 (M+H)+.

Workup

  1. customThe reaction contents
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic phases were washed sequentially with H2O and brine
  4. dry with materialwere dried over Na2SO4
  5. concentrationConcentration
  6. customunder reduced pressure and purification on silica (hexanes/EtOAc, 4:1)

Sources & evidence

ORD record
ord-288e868596b448a7acf505b5eb4c6328
Source dataset
uspto-grants-2003_06
Patent number
US06573272B1

Reaction notes

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