Borane;tetrahydrofuran → HCID 57551835, compound

HRID 907329Notes

Reaction equation

HRID 907329 reaction equation
[CH:1]1([NH:4][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH3:31])=[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][CH:25]3[CH2:27][CH2:26]3)[CH:17]=[C:16]4[C:28](O)=[O:29])[CH:12]=2)=[O:6])[CH2:3][CH2:2]1.O1CCCC1.B>C1COCC1>[CH:1]1([NH:4][C:5](=[O:6])[C:7]2[CH:8]=[CH:9][C:10]([CH3:31])=[C:11]([C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19](=[O:23])[N:18]([CH2:24][CH:25]3[CH2:26][CH2:27]3)[CH:17]=[C:16]4[CH2:28][OH:29])[CH:12]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 575517606-(5-(Cyclopropylcarbamoyl)-2-methylphenyl)-2-(cyclopropylmethyl)-1-oxo-1,2-dihydroisoquinoline-4-carboxylic acid

Product 1

HCID 57551835HCID 57551835, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product of Example 37 step v) (500 mg) in THF (12 mL) at 0° C. was added borane tetrahydrofuran complex (1M/THF) (1.6 mL) dropwise. The ice bath was removed once gas evolution had ceased, and the reaction was stirred at room temperature for 1 hour. The reaction mixture was cooled to 0° C. and further borane tetrahydrofuran complex (1M/THF, 750 uL) was added, and the reaction was slowly warmed to room temperature and stirred for 1 hour. The reaction mixture was quenched with water (50 mL) and extracted into ethyl acetate (2×50 mL). The combined organics were dried over magnesium sulfate, filtered and evaporated in vacuo. Purification (SiO2 chromatography, 3% methanol in dichloromethane) gave the sub-titled compound (300 mg).

Workup

  1. customThe ice bath was removed once gas evolution
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. additionfurther borane tetrahydrofuran complex (1M/THF, 750 uL) was added
  4. temperaturethe reaction was slowly warmed to room temperature
  5. stirringstirred for 1 hour
  6. customThe reaction mixture was quenched with water (50 mL)
  7. extractionextracted into ethyl acetate (2×50 mL)
  8. dry with materialThe combined organics were dried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo
  11. customPurification (SiO2 chromatography, 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-420a3e42730e45739b678c0d25300998
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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