ChemicalBook CAS DataBase List D-Proline, 4-hydroxy-1-(phenylmethyl)-, methyl ester, (4R)-

D-Proline, 4-hydroxy-1-(phenylmethyl)-, methyl ester, (4R)- synthesis

7synthesis methods

Product Name:D-Proline, 4-hydroxy-1-(phenylmethyl)-, methyl ester, (4R)-
CAS Number:114676-53-8
Molecular formula:C13H17NO3
Molecular Weight:235.279

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D-Proline, 4-hydroxy-, methyl ester, hydrochloride (1:1), (4R)-

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D-Proline, 4-hydroxy-1-(phenylmethyl)-, methyl ester, (4R)-

114676-53-8
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Yield:114676-53-8 233.4 g

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in chloroform at 0 - 75; for 1 h;

Steps:

B Step B. Methyl (2R,4R)-1-benzyl-4-hydroxpyrrolidine-2-carboxylate

Methyl (2R,4R)-4-hydroxypyrrolidine-2-carboxylate hydrochloride (1.19 mol) was suspended in CHCl₃ (2 L) in four-neck flask equipped with mechanical stirrer, reflux condenser, dropping funnel and septum and was cooled to 0° C. DIPEA (520 mL, 2.98 mol) was added dropwise at 0° C. and the reaction mixture was warmed to room temperature.
Benzyl bromide (141.7 mL, 1.19 mol) was added dropwise for 1 h.
The reaction mixture was heated to reflux (75° C., oil bath temp.) for 1 h and cooled to room temperature (water bath with crushed ice).
Water (1 L) was added to the reaction mixture and layers were separated.
Organic layer was washed with water (1*1 L), 1M NaOH (1*1 L), brine (1*1 L), dried over MgSO4, filtered and concentrated under reduced pressure to give 233.4 g (83%, after 2 steps) of the desired as a pale orange oil. ESI+MS m/z=235.95 (M+1)⁺; ¹H NMR (700 MHz, CDCl₃) δ 7.32-7.23 (m, 4H), 4.24 (m, 1H), 3.86 (d, J=13.1 Hz, 1H), 3.71 (d, J=13.1 Hz, 1H), 3.63 (s, 1H), 3.34 (dd, J=10.1, 3.8 Hz, 1H), 3.11 (d, J=10.7 Hz, 1H), 3.01 (dt, J=9.9, 1.6 Hz, 1H), 2.63 (dd, J=10.1, 3.8 Hz, 1H), 2.37 (ddd, J=14.2, 10.0, 5.7 Hz, 1H), 1.95 (m, 1H).

References:

US2019/300525,2019,A1 Location in patent:Paragraph 0448; 0451; 0452

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