Ethyl bromoacetate → HCID 90241046, compound

HRID 1777178Notes

Reaction equation

HRID 1777178 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2.C([O-])([O-])=O.[K+].[K+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>CC#N>[CH2:30]([O:29][C:27]([CH2:26][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)=[O:28])[CH3:31]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 10538586tert-Butyl 5-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 90241046HCID 90241046, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl 3,4-dihydro-5-hydroxyisoquinoline-2(1H)-carboxylate (750 mg, 3.01 mmol) and K2CO3 (498 mg, 3.61 mmol) in MeCN was added ethyl 2-bromoacetate (603 mg, 3.61 mmol). The mixture was stirred at room temperature overnight, the mixture was then filtered and the filtrate was concentrated under vacuum to give the desired product (900 mg, 90%). LCMS (m/z): 336.2 [M+H]+.

Workup

  1. filtrationthe mixture was then filtered
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-11ac80ecd0964da59f8c6cb1b56711af
Source dataset
uspto-grants-2016_02
Patent number
US09266836B2

Reaction notes

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