1,4-Dioxane hydrochloride → 4,4-Difluoroproline

HRID 2047688Notes

Reaction equation

HRID 2047688 reaction equation
C(OC([N:8]1[CH2:12][C:11]([F:14])([F:13])[CH2:10][C@H:9]1[C:15]([OH:17])=[O:16])=O)(C)(C)C.O1CCOCC1.Cl>CO>[F:13][C:11]1([F:14])[CH2:12][NH:8][C@H:9]([C:15]([OH:17])=[O:16])[CH2:10]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 22977458(2S)-1-[(tert-butoxy)carbonyl]-4,4-difluoropyrrolidine-2-carboxylic acid

Product 1

HCID 152161024,4-Difluoroproline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-1-(tert-butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid (500 mg, 1.99 mmol) in methanol (30 mL) was added 4N HCl dioxane (3 mL). The reaction mixture was stirred at rt for 6 h. Concentration gave an oil which was used for the next step without purification (480 mg, 100%). 1H NMR (CD3OD, 400 MHz) δ 4.76 (1H, t, J=8.5 Hz), 3.79-3.87 (2H, m), 2.91-3.03 (1H, m), 2.73-2.82 (1H, m).

Workup

  1. concentrationConcentration
  2. customgave an oil which
  3. customwas used for the next step without purification (480 mg, 100%)

Sources & evidence

ORD record
ord-3f62f7e7964c4bd48a5cd1c391725d88
Source dataset
uspto-grants-2013_11
Patent number
US08592579B2

Reaction notes

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