Sodium Bicarbonate → HCID 58980888, compound

HRID 715914Notes

Reaction equation

HRID 715914 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([F:13])[CH2:10][C@H:9]1[C:14](O)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.O1CCCC1.C(=O)(O)[O-].[Na+]>O1CCCC1>[F:13][C@@H:11]1[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C@H:9]([CH2:14][OH:15])[CH2:10]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 2756017(4S)-1-tert-Butoxycarbonyl-4-fluoro-L-proline

Product 1

HCID 58980888HCID 58980888, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4S)-1-tert-butoxycarbonyl-4-fluoropyrrolidine-2-carboxylic acid (4.7 g) in tetrahydrofuran (40 ml), a borane-tetrahydrofuran complex (0.95 M solution in tetrahydrofuran, 31.6 ml) was added under ice cooling, and the mixture was stirred at room temperature for 1 hour. Ice water and a saturated aqueous solution of sodium bicarbonate were added to the reaction solution, followed by extraction with ethyl acetate. The extract was washed with saturated saline and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain the title compound (4.2 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-e6833247bfaa44bfbcdf0c80358fcc40
Source dataset
uspto-grants-2015_11
Patent number
US09187489B2

Reaction notes

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