4-Methylmorpholine → HCID 22176271, compound

HRID 1797491Notes

Reaction equation

HRID 1797491 reaction equation
[CH2:1]([O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16](O)=[O:17])[CH:14]=2)[C:9](=[O:19])[N:8]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:7]=1[CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:2][CH2:3][CH3:4].CN1CCOCC1.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.O>[C:29]([O:28][C:26](=[O:27])[NH:25][CH2:24][C:7]1[N:8]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:9](=[O:19])[C:10]2[C:15]([C:6]=1[O:5][CH2:1][CH2:2][CH2:3][CH3:4])=[CH:14][C:13]([CH2:16][OH:17])=[CH:12][CH:11]=2)([CH3:32])([CH3:30])[CH3:31]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 22176086HCID 22176086, compound

Product 1

HCID 22176271HCID 22176271, compoundYield 76.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-butoxy-3-{{(tert-butoxycarbonyl)-amino}methyl}-2-isobutyl-1-oxo-1,2-dihydro-6-isoquinolinecarboxylic acid (synthesized according to the method similar to that in Example 76 (1)) (0.45 g, 3.5 mmol) and N-methylmorpholine (0.13 ml, 1.2 mmol) in tetrahydrofuran (10 ml) was added ethyl chloroformate (0.12 ml, 1.2 mmol) at 0° C., and the mixture was stirred at 0° C. for 10 min. To the obtained mixture was added sodium tetrahydroborate (0.11 g, 3 mmol) and the mixture was stirred at 0° C. 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 recrystallized from ethyl acetate-diisopropyl ether to give tert-butyl(4-butoxy-6-hydroxymethyl-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinyl)methylcarbamate (0.33 g, 76.7%) as crystals.

Workup

  1. stirringthe mixture was stirred at 0° C. for 1 h
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-8be17ebcff604666b320e3626a910df1
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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