4-Methylmorpholine → HCID 22175460, compound

HRID 1797562Notes

Reaction equation

HRID 1797562 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[N:11]([CH2:30][CH:31]([CH3:33])[CH3:32])[C:12](=[O:29])[C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:17][C:16]([C:26](O)=[O:27])=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC)=O.[BH4-].[Na+]>O1CCCC1.O.CO>[C:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][C:10]1[N:11]([CH2:30][CH:31]([CH3:32])[CH3:33])[C:12](=[O:29])[C:13]2[C:18]([C:19]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[CH:17][C:16]([CH2:26][OH:27])=[CH:15][CH:14]=2)([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 22175400HCID 22175400, compound

Product 1

HCID 22175460HCID 22175460, compoundYield 77.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-[[(tert-butoxycarbonyl)amino]methyl]-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-6-isoquinolinecarboxylic acid (6.31 g, 14 mmol) and N-methylmorpholine (1.8 mL, 16.8 mmol) in tetrahydrofuran (50 mL) was added ethyl chloroformate (1.6 mL, 16.8 mmol) at 0° C. and the mixture was stirred at 0° C. for 10 min. To the obtained mixture were added sodium tetrahydroborate (1.59 g, 42 mmol) and methanol (5 mL) 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 precipitated crystals were recrystallized from ethyl acetate-diisopropyl ether to give tert-butyl(6-hydroxymethyl-2-isobutyl-1-oxo-4-phenyl-1,2-dihydro-3-isoquinolinyl)methylcarbamate (4.73 g, 77.4%) 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 precipitated crystals were recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-74dd181f4ecf4356b24dab5d0f639561
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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