1-Cbz-3-aminomethyl-3-hydroxypyrrolidine synthesis
- Product Name:1-Cbz-3-aminomethyl-3-hydroxypyrrolidine
- CAS Number:872715-55-4
- Molecular formula:C13H18N2O3
- Molecular Weight:250.29
872715-54-3
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872715-55-4
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Yield:872715-55-4 79%
Reaction Conditions:
Stage #1: (+/-)-phenylmethyl 3-cyano-3-hydroxy-1-pyrrolidinecarboxylatewith lithium aluminium tetrahydride in tetrahydrofuran at 20; for 24 h;
Stage #2: with sodium hydroxide;water in tetrahydrofuran;
Steps:
41.b
b) (+/-)-phenylmethyl 3-(aminomethyl)-3-hydroxy-1 -pyrrolidinecarboxylate; To a stirred solution of phenylmethyl 3-cyano-3-hydroxy-1 -pyrrolidinecarboxylate (0.92 g, 3.74 mmole), in THF (50 mL) at RT was added LiAIH4 (3.75 ml_, 1M in THF). After 24h, the reaction was quenched with H2O (0.15 mL), 20% NaOH (0.30 mL) and then H2O (0.35 mL).The reaction contents were filtered through a scinter-glass funnel and concentrated under vacuum to afford the title compound (0.50 g, 79%) as a yellow oil: LC- MS (ES) m/e 250 (M + H)+.
References:
WO2006/2047,2006,A2 Location in patent:Page/Page column 138