Hydrochloric Acid → HCID 22176154, compound

HRID 1797528Notes

Reaction equation

HRID 1797528 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:13]([C:24](O)=[O:25])=[C:12]2[O:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[BH4-].[Na+].Cl>O1CCCC1.CN(C)C=O.COCCOC>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:13]([CH2:24][OH:25])=[C:12]2[O:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 4311764Sodium borohydrideHCID 22176375HCID 22176375, compound

Product 1

HCID 22176154HCID 22176154, compoundYield 96.5%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 6-benzyloxy-4-butoxy-2-isobutyl-1-oxo-1,2-dihydro-3-isoquinolinecarboxylic acid (7.62 g, 18 mmol) in tetrahydrofuran (50 mL) were added oxalyl chloride (1.9 mL, 21.6 mmol) and N,N-dimethylformamide (2 drops), and the mixture was stirred at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in tetrahydrofuran (30 mL). The obtained solution was added dropwise to a suspension of sodium tetrahydroborate (2.38 g, 63 mmol) in 1,2-dimethoxyethane (50 mL) at 0° C. The obtained mixture was stirred at 0° C. for 1 h. The reaction mixture was poured into 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained crystals were recrystallized from ethyl acetate-diisopropyl ether to give 6-benzyloxy-4-butoxy-3-hydroxymethyl-2-isobutyl-1(2H)-isoquinolinone (7.11 g, 96.5%) as crystals.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in tetrahydrofuran (30 mL)
  3. stirringThe obtained mixture was stirred at 0° C. for 1 h
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained crystals were recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-70bed3da63b14671ae0c648efc5ac9d8
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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