Water → 1,3,4,9-Tetrahydro-beta-carboline-2-carboxylic acid benzyl ester

HRID 1063237Notes

Reaction equation

HRID 1063237 reaction equation
[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[CH2:14]([O:21][C:22](ON1C(=O)CCC1=O)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.O>CN(C=O)C>[CH2:14]([O:21][C:22]([N:2]1[CH2:3][CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[CH2:1]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 107838Tetrahydro-beta-carboline

Product 1

HCID 110667371,3,4,9-Tetrahydro-beta-carboline-2-carboxylic acid benzyl esterYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole (20.0 g, 116.2 mmole) in dry DMF (150 mL) at RT was added N-(benzyloxycarbonyloxy)succinimide (31.84 g, 127.76 mmole) and triethylamine (13.0 g. 127.76 mmole). After 12 h, the reaction contents were poured into H2O (150 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 yellow oil. Purification on silica (hexanes/EtOAc, 4:1) afforded the title compound (34.48 g. 97%) as a white solid: MS (ES) m/e 307 (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 yellow oil
  7. customPurification on silica (hexanes/EtOAc, 4:1)

Sources & evidence

ORD record
ord-3be1b3c554584e3db11dbeca174b09fc
Source dataset
uspto-grants-2005_11
Patent number
US06964970B2

Reaction notes

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