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Chemical Structure| 344-25-2 Chemical Structure| 344-25-2
Chemical Structure| 344-25-2

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D-proline is an isomer of the naturally occurring amino acid, L-Proline.

Synonyms: (+)-(R)-Proline; (R)-(+)-Proline; (R)-Proline

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Product Details of D-Proline

CAS No. :344-25-2
Formula : C5H9NO2
M.W : 115.13
SMILES Code : O=C(O)[C@@H]1NCCC1
Synonyms :
(+)-(R)-Proline; (R)-(+)-Proline; (R)-Proline
MDL No. :MFCD00064317
InChI Key :ONIBWKKTOPOVIA-SCSAIBSYSA-N
Pubchem ID :8988

Safety of D-Proline

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of D-Proline

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 344-25-2 ]
  • Downstream synthetic route of [ 344-25-2 ]

[ 344-25-2 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 75-87-6 ]
  • [ 344-25-2 ]
  • [ 1263774-42-0 ]
YieldReaction ConditionsOperation in experiment
0.23 g at 20℃; for 8 h; To a solution of D-proline (0.4 g, 3.48 mmol) in MeCN (8 ml) the trifluoroacetaldehyde (0.68 ml, 6.94 mmol) was added and the resulting mixture was stirred at RT for 8 hrs. Solvents were evaporated and the residue was triturated with diethyl ether. After solvent filtration and drying, 0.23 g of title compound (D48) was isolated. MS: (ES/+) m/z: 244.0 [MH+] C7H8CI3N02 requires 242.96 1 H NMR (400MHz ,CHCI3-d) δ (ppm): 4.15 (dd, J = 4.5, 8.6 Hz, 1 H), 3.52 - 3.36 (m, J = 7.0, 7.0, 10.5 Hz, 1 H), 3.22 - 3.07 (m, 1 H), 2.33 - 2.20 (m, 1 H), 2.19 - 2.08 (m, 1 H), 1 .96 (quind, J = 5.9, 12.1 Hz, 1 H), 1 .84 - 1 .69 (m, 1 H), 1 .61 (br. s., 1 H).
0.23 g at 20℃; for 8 h; Description 1: (7aR)-3-(trichloromethyl)tetrahydropyrrolo[1,2-c]oxazol-1(3H)-one (D1) [0259] [0260] To a solution of D-proline (0.4 g, 3.48 mmol) in MeCN (8 ml) the trifluoroacetaldehyde (0.68 ml, 6.94 mmol) was added and the resulting mixture was stirred at RT for 8 hrs. Solvents were evaporated and the residue was triturated with diethyl ether. After solvent filtration and drying, 0.23 g of title compound (D1) was isolated. [0261] MS: (ES/+) m/z: 244.0 [MH+] C7H8Cl3NO2 requires 242.96 [0262] 1H NMR (400 MHz, CHCl3-d) δ (ppm): 4.15 (dd, J=4.5, 8.6 Hz, 1H), 3.52-3.36 (m, J=7.0, 7.0, 10.5 Hz, 1H), 3.22-3.07 (m, 1H), 2.33-2.20 (m, 1H), 2.19-2.08 (m, 1H), 1.96 (quind, J=5.9, 12.1 Hz, 1H), 1.84-1.69 (m, 1H), 1.61 (br. s., 1H).
0.23 g at 20℃; for 8 h; To a solution of D-proline (0.4 g, 3.48 mmol) in MeCN (8 ml) the trifluoroacetaldehyde (0.68 ml, 6.94 mmol) was added and the resulting mixture was stirred at RT for 8 hrs. Solvents were evaporated and the residue was triturated with diethyl ether. After solvent filtration and drying, 0.23 g of title compound (D48) was isolated.MS: (ES/+) m/z: 244.0 [MH+] C7H8Cl3NO2 requires 242.961H NMR (400 MHz, CHCl3-d) δ (ppm): 4.15 (dd, J=4.5, 8.6 Hz, 1H), 3.52-3.36 (m, J=7.0, 7.0, 10.5 Hz, 1H), 3.22-3.07 (m, 1H), 2.33-2.20 (m, 1H), 2.19-2.08 (m, 1H), 1.96 (quind, J=5.9, 12.1 Hz, 1H), 1.84-1.69 (m, 1H), 1.61 (br. s., 1H).
References: [1] Patent: US2011/136778, 2011, A1, . Location in patent: Page/Page column 54.
[2] Patent: WO2013/4290, 2013, A1, . Location in patent: Page/Page column 66.
[3] Patent: US2014/243373, 2014, A1, . Location in patent: Paragraph 0259-0261.
[4] Patent: US2015/87626, 2015, A1, . Location in patent: Paragraph 0504; 0505; 0506; 0507.
 

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