Ethyl bromoacetate → Ethyl (2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetate

HRID 2236095Notes

Reaction equation

HRID 2236095 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:20][CH2:19][C:11]2[NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>CC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:20][CH2:19][C:11]2[N:12]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 46344376tert-Butyl 1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

Product 1

HCID 71063767Ethyl (2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl)-acetateYield 70.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred suspension of crude 2-tert.-butoxycarbonyl-1,2,3,4-tetrahydro-pyrido[4,3-b]indol (33.5 mmol) and caesium carbonate (25.1 g, 77.1 mmol) in dry acetone is added ethyl bromoacetate (5.6 ml, 50.3 mmol). The reaction mixture is stirred at rt overnight and then filtered over a small plug of Celite. The filtrate is concentrated under reduced pressure and the residue is purified by silica gel column chromatography (hexane/EtOAc 5:1) to afford pure sub-title compound as yellow oil (8.45 g) in 70% yield (over two steps). tR (LC-2) 2.46 min; ESI-MS (positive ion): m/z 381.54 [M+Na]+ (calcd 358.43 for C20H26N2O4).

Workup

  1. filtrationfiltered over a small plug of Celite
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customthe residue is purified by silica gel column chromatography (hexane/EtOAc 5:1)

Sources & evidence

ORD record
ord-5e5eed469a0a4ba69de330b73d6eba4a
Source dataset
uspto-grants-2010_05
Patent number
US07714132B2

Reaction notes

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