Hydrochloric Acid → 1-((Tert-butoxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid

HRID 354433Notes

Reaction equation

HRID 354433 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11]([F:14])([F:13])[CH2:10][CH:9]1[C:15]([O:17]C)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].Cl>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11]([F:13])([F:14])[CH2:10][CH:9]1[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 534019261000313-00-7

Product 1

HCID 235125141-((Tert-butoxy)carbonyl)-4,4-difluoropyrrolidine-2-carboxylic acidYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 1-(tert-butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylate (885 mg, 3.34 mmol) in THF (25 ml) was added 0.25 N NaOH (26.7 ml, 6.67 mmol) and the stirring was continued for 1 h. The mixture was poured into 1 N HCl (100 ml) and extracted with CHCl3 (2×200 ml). The combined extracts were washed with brine (100 ml), dried over MgSO4, and evaporated to give 1-(tert-butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid (775 mg, 92%) as a yellow crystalline solid. mp 113-117° C.; 1H-NMR (CDCl3) δ1.44 and 1.49 (s, each, total 9 H), 2.53-2.80 (m, 2 H), 3.71-3.90 (m, 2 H), 4.20-4.61 (m, 1 H); MS (FAB) m/z, 252 (M++1); Anal. Calcd. for C10H15F2O4: C, 47.81; H, 6.02; N, 5.58. Found: C, 48.06; H, 6.05; N, 5.45.

Workup

  1. extractionextracted with CHCl3 (2×200 ml)
  2. washThe combined extracts were washed with brine (100 ml)
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-11555cc5465248938a16a3782eb76909
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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