Benzyl succinimido carbonate → 1,3,4,9-Tetrahydro-beta-carboline-2-carboxylic acid benzyl ester

HRID 2063727Notes

Reaction equation

HRID 2063727 reaction equation
[CH2:1]([O:8][C:9]([O:11]N1C(=O)CCC1=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]1[C:31]2[NH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]=2[CH2:22][CH2:21][NH:20]1>O1CCCC1>[CH2:1]([O:8][C:9]([N:20]1[CH2:21][CH2:22][C:23]2[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[NH:30][C:31]=2[CH2:19]1)=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 107838Tetrahydro-beta-carboline

Product 1

HCID 110667371,3,4,9-Tetrahydro-beta-carboline-2-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-(benzyloxycarbonyloxy)succinimide (9.61 g, 38.6 mmol) in anhydrous tetrahydrofuran (30 ml) was added to a suspension of 2,3,4,9-tetrahydro-1H-β-carboline (4.43 g, 25.7 mmol) and 4-N,N-dimethylaminopyridine (266 mg) in anhydrous tetrahydrofuran (30 ml), while cooling with ice. The suspension was stirred at room temperature for 16 h and the tetrahydrofuran was then removed i. vac. The residue was dissolved in ethyl acetate (20 ml) and the solution was washed with water (2×20 ml). The organic phase was dried with sodium sulfate and concentrated i. vac. The crude product (11.0 g) was purified by flash chromatography with cyclohexane/ethyl acetate (4:1).

Workup

  1. temperaturewhile cooling with ice
  2. customthe tetrahydrofuran was then removed i
  3. dissolutionThe residue was dissolved in ethyl acetate (20 ml)
  4. washthe solution was washed with water (2×20 ml)
  5. dry with materialThe organic phase was dried with sodium sulfate
  6. concentrationconcentrated i
  7. customThe crude product (11.0 g) was purified by flash chromatography with cyclohexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-89859c59463944c2b2a9f937531fe7b9
Source dataset
uspto-grants-2012_10
Patent number
US08288406B2

Reaction notes

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