ChemicalBook CAS DataBase List 1-BENZYLPYRROLIDIN-3-YL-METHANOL

1-BENZYLPYRROLIDIN-3-YL-METHANOL synthesis

10synthesis methods

Product Name:1-BENZYLPYRROLIDIN-3-YL-METHANOL
CAS Number:5731-17-9
Molecular formula:C12H17NO
Molecular Weight:191.27

METHYL N-BENZYL-3-PYRROLIDINECARBOXYLATE

17012-21-4
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$14.00/1g

5731-17-9
127 suppliers
$37.00/1g

Yield: 88%

Reaction Conditions:

with sodium sulfate in tetrahydrofuran

Steps:

5.A A.
A. 1-Benzylpyrrolidine-3-methanol To a mixture of methyl 1-benzylpyrrolidine-3-carboxylate (11.67 g, 50 mmol) and tetrahydrofuran, at 0° C. was added lithium aluminum hydride (3.795 g, 100 mmol). The reaction was warmed to room temperature and refluxed for 24 hours. After cooling to 0° C., the reaction was quenched with saturated sodium sulfate and warmed to room temperature. Tetrahyrofuran (50 mL) and solid sodium sulfate were added to the mixture. After stirring for 1 hour, the mixture was filtered and the filtrate was concentrated and vacuum dried for 3 days to give the title compound as a colorless oil (8.49 g, 88%). ¹H-NMR (300 MHz, DMSO-d₆): 7.21-7.31 (m, 5H), 4.50 (t, J=5.3 Hz, 1H), 3.51 (s, 2H), 3.20-3.31 (m, 2H), 2.35-2.50 (m, 4H), 2.10-2.27 (m, 1H), 1.70-1.85 (m, 1H), 1.27-1.43 (m, 1H). IS-MS, m/e: 192.4 (m+1).

References:

Eli Lilly and Company US6635657, 2003, B1