Lithium triethylborohydride → HCID 118069378, compound

HRID 920857Notes

Reaction equation

HRID 920857 reaction equation
[C:1]([C:4]1[C:5]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[C:29]([Cl:34])[CH:28]=2)=[N:6][N:7]2[CH:12]([CH2:13][CH2:14]OS(C)(=O)=O)[CH2:11][N:10]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:9][C:8]=12)(=[O:3])[NH2:2].[Li+].[B-](CC)(CC)CC>C1COCC1>[C:1]([C:4]1[C:5]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[C:29]([Cl:34])[CH:28]=2)=[N:6][N:7]2[CH:12]([CH2:13][CH3:14])[CH2:11][N:10]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:9][C:8]=12)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 23712863Lithium triethylborohydrideHCID 118062528HCID 118062528, compound

Product 1

HCID 118069378HCID 118069378, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl 3-carbamoyl-2-(3-chloro-4-fluorophenyl)-7-(2-((methylsulfonyl)oxy)ethyl)-6,7-dihydropyrazolo[1,5-a]pyrazine-5(4H)-carboxylate (200 mg, 0.387 mmol) in THF (6 mL) at 0° C. under nitrogen was added 1M THF solution of SUPER-HYDRIDE® (1.934 mL, 1.934 mmol). The reaction mixture was stirred at RT for 1 h and quenched with water. It was extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and filtered. The filtrate was concentrated. The crude product was purified by silica gel chromatography (40 g REDISEP® column, eluting with 35-80% EtOAc in hexane). Fractions containing the product were combined and evaporated to afford Intermediate A98B (128 m g, 78%). MS(ES): m/z=423.1 [M+H]+.

Workup

  1. customquenched with water
  2. extractionIt was extracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customThe crude product was purified by silica gel chromatography (40 g REDISEP® column, eluting with 35-80% EtOAc in hexane)
  8. additionFractions containing the product
  9. customevaporated
  10. customto afford Intermediate A98B (128 m g, 78%)

Sources & evidence

ORD record
ord-0f70d07a041a4d70a3a2fe2a304f5008
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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