| Identification | Back Directory | [Name]
L-Proline, 4,4-difluoro- (9CI) | [CAS]
52683-81-5 | [Synonyms]
4,4-difluoroproline
4,4-difluoro-L-Proline
L-Proline, 4,4-difluoro-
L-Proline, 4,4-difluoro- (9CI)
(S)-4,4-Difluoropyrrolidine-2-carboxylic acid
(2S)-4,4-Difluoropyrrolidine-2-carboxylic acid | [Molecular Formula]
C5H7F2NO2 | [MDL Number]
MFCD10697866 | [MOL File]
52683-81-5.mol | [Molecular Weight]
151.111 |
| Chemical Properties | Back Directory | [Boiling point ]
254.0±40.0 °C(Predicted) | [density ]
1.41±0.1 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [pka]
1.40±0.40(Predicted) | [Appearance]
White to off-white Solid |
| Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of (S)-4,4-difluoropyrrolidine-2-carboxylic acid from N-Boc-4,4-difluoro-L-proline:
1. (S)-1-(tert-butoxycarbonyl)-4,4-difluoropyrrolidine-2-carboxylic acid (500 mg, 1.99 mmol) was dissolved in methanol (30 mL).
2. To the above solution was added a dioxane solution (3 mL) of 4N HCl.
3. The reaction mixture was stirred at room temperature for 6 hours.
4. Upon completion of the reaction, the reaction solution was concentrated to give an oily product (480 mg, 100% yield), which could be used in the next step without further purification. 5. The structure of the product was determined by 1H NCl and the reaction was carried out in aqueous solution.
5. The structure of the product was confirmed by 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). | [References]
[1] Patent: US2008/9497, 2008, A1. Location in patent: Page/Page column 109
[2] Patent: WO2014/82379, 2014, A1. Location in patent: Page/Page column 158; 159; 163
[3] Tetrahedron Letters, 1998, vol. 39, # 10, p. 1169 - 1172 |
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Cool Pharm, Ltd
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www.coolpharm.com |
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