TRANS-4-HYDROXY-D-PROLINE HYDROCHLORIDE
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TRANS-4-HYDROXY-D-PROLINE HYDROCHLORIDE
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CAS No:
142347-81-7
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Formula:
C5H10ClNO3
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Chemical Name:
TRANS-4-HYDROXY-D-PROLINE HYDROCHLORIDE
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Synonyms:
trans-4-Hydroxypyrrolidine-2-carboxylic acid hydrochloride;HCl.trans-D-Hyp-OH;trans-D-Hpy-OH.HCl;D-Proline, 4-hydroxy-, hydrochloride (1:1), (4S)-;(4S)-4-Hydroxy-D-proline HCl;trans-4-Hydroxy-D-proline HCl;D-Proline, 4-hydroxy-,hydrochloride, trans-;(2R,4S)-(+)-4-Hydroxy-D-proline Hydrochloride
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CAS No:
Safety Information
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
H315
TRANS-4-HYDROXY-D-PROLINE HYDROCHLORIDE Use and Manufacturing
(2R, 45)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride[839] To a suspension of iraws-4-hydroxy-D-proline hydrochloride (150 g, 0.89 mol, 1 equivalent) in methanol (1.25 L), thionyl chloride (130 mL, 1.79 mol, 2 equivalents) was added drop-wise at 0-5 °C. Then the reaction mixture was stirred for 4 hours at 20- 25 °C. The reaction mixture was concentrated under reduced pressure. This crude material was stirred in a mixture of ethanol-methyl tert-butyl ether (1:4, 750 mL) for 30 minutes and the solid was collected by filtration. The wet cake was dried in a vacuum tray dryer for 8 hours at about 50 °C to afford the title compound. lR NMR (300 MHz, DMSO-i?) ' ppm 2.03 -2.23 (m, 2H), 3.06 (d, 1H, J=12.0Hz), 3.37 (dd, 2H, J=4.5Hz, J=12.0Hz), 3.75 (s, 3H), 4.41- 4.48 (m, 2H), 5.64 (bs, 1H), 9.43 (bs, 1H), 10.48 (bs, 1H).Example 17A[0833] (2R, 45)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride[0834] To a suspension of iraws-4-hydroxy-D-proline hydrochloride (150 g, 0.89 mol, 1 equivalent) in methanol (1.25 L), thionyl chloride (130 mL, 1.79 mol, 2 equivalents) was added drop-wise at 0-5 °C. Then the reaction mixture was stirred for 4 hours at 20-25 °C. The reaction mixture was concentrated under reduced pressure. This crude material was stirred in a mixture of ethanol-methyl tert-butyl ether (1 :4, 750 mL) for 30 minutes and the solid was collected by filtration. The wet cake was dried in a vacuum tray dryer for 8 hours at about 50 °C to afford the title compound. XH NMR (300 MHz, DMSO-i¾) delta ppm 2.03 -2.23 (m, 2H), 3.06 (d, 1H, J=12.0Hz), 3.37 (dd, 2H, J=4.5Hz, J=12.0Hz), 3.75 (s, 3H), 4.41- 4.48 (m, 2H), 5.64 (bs, 1H), 9.43 (bs, 1H), 10.48 (bs, 1H).
Hydroxyprolines can be used as chiral building blocks in the synthesis of pharmaceuticals.
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TRANS-4-HYDROXY-D-PROLINE HYDROCHLORIDE
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