Water → HCID 22175781, compound

HRID 1797494Notes

Reaction equation

HRID 1797494 reaction equation
[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:16]C(=O)OCC3C4C=CC=CC=4C4C3=CC=CC=4)[CH:14]=2)[C:9](=[O:34])[N:8]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:7]=1[CH2:39][NH:40][C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:2][CH2:3][CH3:4].N1CCCC1.O>CN(C)C=O>[C:44]([O:43][C:41](=[O:42])[NH:40][CH2:39][C:7]1[N:8]([CH2:35][CH:36]([CH3:38])[CH3:37])[C:9](=[O:34])[C:10]2[C:15]([C:6]=1[O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)([CH3:47])([CH3:45])[CH3:46]

Participants

5

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 69365248HCID 69365248, compound

Product 1

HCID 22175781HCID 22175781, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 9H-fluoren-9-ylmethyl 4-butoxy-3-{{(tert-butoxycarbonyl)amino}methyl}-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinylcarbamate (0.45 g, 0.7 mmol) in N,N-dimethylformamide (10 ml) was added pyrrolidine (0.5 ml) and the mixture was stirred at room temperature for 1 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl(6-amino-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.23 g, 79.3%) as crystals.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-eb5f3099a4a14ce89fc59a2aa3688f2c
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

Loading…