Lithium borohydride → HCID 59410112, compound

HRID 1805157Notes

Reaction equation

HRID 1805157 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-4676605bb3794c41b30604efa2c44746
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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