Lithium borohydride → HCID 59410112, compound

HRID 2404895Notes

Reaction equation

HRID 2404895 reaction equation
[Li+].[BH4-].[F:3][C:4]1([F:26])[CH2:8][N:7]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([C:18]([F:21])([F:20])[F:19])[CH:10]=2)[C@H:6]([C:22](OC)=[O:23])[CH2:5]1>C1COCC1.C(OCC)(=O)C>[F:26][C:4]1([F:3])[CH2:8][N:7]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11]([C:18]([F:20])([F:21])[F:19])[CH:10]=2)[C@H:6]([CH2:22][OH:23])[CH2:5]1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 59410118HCID 59410118, compound

Product 1

HCID 59410112HCID 59410112, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of LiBH4 (55 mg, 2.54 mmol) in anhydrous THF (3 mL) was added a solution of (S)-methyl 4,4-difluoro-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine-2-carboxylate (300 mg, 0.85 mmol) in anhydrous THF at 0° C. The reaction mixture was stirred at 0° C. for 20 min then allowed to come to room temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate (100 mL), washed with water (50 mL), and then brine. The layers were separated, and the organic layer was dried over Na2SO4, filtered, and concentrated to afford (S)-(4,4-difluoro-1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidin-2-yl)methanol as a yellow, viscous oil (275 mg, 100%). LC/MS: m/z 327.2 (M+H)+ at 1.54 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customto come to room temperature
  2. stirringstirred overnight
  3. washwashed with water (50 mL)
  4. customThe layers were separated
  5. dry with materialthe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-40fdb9e00687492287c3f6fd6890bb87
Source dataset
uspto-grants-2014_08
Patent number
US08802700B2

Reaction notes

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