Hydrochloric Acid → HCID 22500572, compound

HRID 1815450Notes

Reaction equation

HRID 1815450 reaction equation
[I-].[CH3:2][N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH2:10][CH2:11][N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[CH2:4]1.[BH4-].[Na+].Cl.[OH-].[Na+]>CO.O>[CH3:2][N:3]1[CH2:8][CH2:7][CH2:6][CH:5]([CH2:9][CH2:10][CH2:11][N:12]2[C:16](=[O:17])[C:15]3=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]3[C:13]2=[O:22])[CH2:4]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 22500429HCID 22500429, compound

Product 1

HCID 22500572HCID 22500572, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (−78° C.) suspension of the product of step b (1.49 g, 3.65 mmol) in methanol (36 ml) was added portionwise sodium borohydride (270 mg, 7.30 mmol) and the resultant suspension stirred at this temperature for 20 minutes. The suspension was allowed to warm to 0° C. and the reaction stirred for a further 30 minutes. The suspension was treated with aqueous 2M hydrochloric acid (3.6 ml) and the stirring was continued for a further 1 h. The reaction mixture was treated with sufficient aqueous 2M sodium hydroxide to pH 11 and water (100 ml) was added. The aqueous phase was extracted thrice with DCM (100 ml) and the combined organic extracts were dried over anhydrous sodium sulfate. The filtrate was evaporated at reduced pressure and the residue was dissolved in methanol (10 ml) and treated with palladium on charcoal (150 mg). The resultant suspension was stirred under a hydrogen atmosphere (via balloon) for 16 h. The suspension was filtered through a pad of celite and the filter-cake was washed with methanol (100 ml). The filtrate was evaporated at reduced pressure and the residue was purified by flash column chromatography (90:10:1 DCM:methanol:ammonia) to obtain the title compound (437 mg, 42%). 1H NMR 7.87-7.82 (2H, m), 7.74-7.69 (2H, m), 3.72-3.65 (2H, m), 2.89-2.82 (2H, m), 2.28 (3H, s), 1.89-0.84 (1H, m).

Workup

  1. temperatureTo a cooled
  2. waitthe stirring was continued for a further 1 h
  3. additionwas added
  4. extractionThe aqueous phase was extracted thrice with DCM (100 ml)
  5. dry with materialthe combined organic extracts were dried over anhydrous sodium sulfate
  6. customThe filtrate was evaporated at reduced pressure
  7. dissolutionthe residue was dissolved in methanol (10 ml)
  8. additiontreated with palladium on charcoal (150 mg)
  9. stirringThe resultant suspension was stirred under a hydrogen atmosphere (via balloon) for 16 h
  10. filtrationThe suspension was filtered through a pad of celite
  11. washthe filter-cake was washed with methanol (100 ml)
  12. customThe filtrate was evaporated at reduced pressure
  13. customthe residue was purified by flash column chromatography (90:10:1 DCM:methanol:ammonia)

Sources & evidence

ORD record
ord-e892863b52dd4f1f8b5ff7de97aa3c3a
Source dataset
uspto-grants-2005_04
Patent number
US06878736B1

Reaction notes

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