Lithium borohydride → HCID 68815110, compound

HRID 732358Notes

Reaction equation

HRID 732358 reaction equation
[BH4-].[Li+].C[O:4][C:5]([C@H:7]1[CH2:11][C@@H:10]([F:12])[CH2:9][N:8]1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=O>C1COCC1>[C:16]([O:15][C:13]([N:8]1[CH2:9][C@H:10]([F:12])[CH2:11][C@@H:7]1[CH2:5][OH:4])=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 68687525(2R,4R)-1-tert-butyl 2-methyl 4-fluoropyrrolidine-1,2-dicarboxylate

Product 1

HCID 68815110HCID 68815110, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add lithium borohydride (1.03 g, 47.4 mmol) to an ice cold solution of 4-(R)-fluoropyrrolidine-N1,2-(R)-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (7.8 g, 31.5 mmol) in THF (100 mL). Let warm to room temperature over 18 h. Cool in ice bath. Slowly add acetic acid (5 mL) and water and extract with ethyl acetate. Wash extract with water, saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with hexanes and ethyl acetate) to give the title compound as a thick oil (5.56 g, 80%).

Workup

  1. temperatureCool in ice bath
  2. extractionSlowly add acetic acid (5 mL) and water and extract with ethyl acetate
  3. washWash
  4. extractionextract with water, saturated aqueous sodium bicarbonate solution, saturated aqueous sodium chloride
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate
  7. custompurify
  8. wash(silica gel chromatography, eluting with hexanes and ethyl acetate)

Sources & evidence

ORD record
ord-f86f6e7cf5fe4df39bb4b58e4ba3e370
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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