9-Fluorenylmethyl chloroformate → 4-[2-(2-hydroxy-ethyl)-1-oxo-1,2-dihydro-isoquinolin-7-yl]piperazine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

HRID 2068596Notes

Reaction equation

HRID 2068596 reaction equation
C([O-])(O)=O.[Na+].[OH:6][CH2:7][CH2:8][N:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][C:13]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[CH:14][CH:15]=2)[C:10]1=[O:25].[CH:26]1[C:38]2[CH:37]([CH2:39][O:40][C:41](Cl)=[O:42])[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]=2[CH:29]=[CH:28][CH:27]=1>O1CCCC1>[CH:26]1[C:38]2[CH:37]([CH2:39][O:40][C:41]([N:22]3[CH2:23][CH2:24][N:19]([C:13]4[CH:12]=[C:11]5[C:16]([CH:17]=[CH:18][N:9]([CH2:8][CH2:7][OH:6])[C:10]5=[O:25])=[CH:15][CH:14]=4)[CH2:20][CH2:21]3)=[O:42])[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:30]=2[CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 343679-Fluorenylmethyl chloroformateHCID 516892Sodium BicarbonateHCID 592382052-(2-Hydroxy-ethyl)-7-piperazin-1yl-isoquinolin-1-one

Product 1

HCID 592381934-[2-(2-hydroxy-ethyl)-1-oxo-1,2-dihydro-isoquinolin-7-yl]piperazine-1-carboxylic acid 9H-fluoren-9-ylmethyl esterYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of sat. aqueous NaHCO3 (80 mL), compound 8 (4.3 g, 15.7 mmol) in tetrahydrofuran was added chloroformic acid 9-fluorenylmethyl ester (1.5 eq.). The mixture was stirred for 2 h at room temperature, then concentrated. The residue was extracted with ethyl acetate, dried (sodium sulfate) and concentrated in vacuo to give 9 (4.6 g, yield 59%).

Workup

  1. concentrationconcentrated
  2. extractionThe residue was extracted with ethyl acetate
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e3669d51d9214a55aabb0f7a57a18aaf
Source dataset
uspto-grants-2012_10
Patent number
US08299023B2

Reaction notes

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