Water → 2-Benzyloxycarbonyl-9-[(4-benzyloxyphenyl)methyl]-1,3,4,9-tetrahydro-2H-pyrido[3,4-b] indole

HRID 1368102Notes

Reaction equation

HRID 1368102 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.[CH2:24]([O:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Cl)=[CH:34][CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[H-].[Na+].O>CN(C=O)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]([CH2:36][C:35]3[CH:38]=[CH:39][C:32]([O:31][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:33][CH:34]=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 4

HCID 962WaterHCID 24758Sodium hydrideHCID 700424-Benzyloxybenzyl chlorideHCID 110667371,3,4,9-Tetrahydro-beta-carboline-2-carboxylic acid benzyl ester

Product 1

HCID 120692912-Benzyloxycarbonyl-9-[(4-benzyloxyphenyl)methyl]-1,3,4,9-tetrahydro-2H-pyrido[3,4-b] indoleYield 93.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-benzyloxycarbonyl-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole (17.75 g, 58.0. mmole) in dry DMF (150 mL) at was added 4-benzyloxybenzylchloride (14.85 g, 63.8 mmole). After 10 min, 60% NaH (2.78 g, 69.6 mmole) was added and the reaction slurry was allowed to warm to RT and stir for 12 hr. The reaction contents were poured into H2O (200 mL) and extracted with EtOAc (2×200 mL). The combined organic phases were washed sequentially with H2O and brine, then were dried over Na2SO4. Concentration under reduced pressure gave a waxy solid. Purification on silica (hexanes/EtOAc, 4:1) afforded the title compound (27.13 g, 93%) as a white solid: MS (ES) m/e 503 (M+H)+.

Workup

  1. customThe reaction contents
  2. extractionextracted with EtOAc (2×200 mL)
  3. washThe combined organic phases were washed sequentially with H2O and brine
  4. dry with materialwere dried over Na2SO4
  5. concentrationConcentration under reduced pressure
  6. customgave a waxy solid
  7. customPurification on silica (hexanes/EtOAc, 4:1)

Sources & evidence

ORD record
ord-be07d8468c0f4df7a3c8ca58361eca1d
Source dataset
uspto-grants-2003_06
Patent number
US06573272B1

Reaction notes

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