ChemicalBook CAS DataBase List 1-Methylpyrrolidine-2-methanol

1-Methylpyrrolidine-2-methanol synthesis

6synthesis methods

Product Name:1-Methylpyrrolidine-2-methanol
CAS Number:3554-65-2
Molecular formula:C6H13NO
Molecular Weight:115.17

50-00-0

498-63-5

3554-65-2

a) A mixture of (RS)-pyrrolidin-2-ylmethanol (1.00 g, 9.90 mmol, 1.0 eq.), 35% aqueous formaldehyde (10 mL) and 10% (1-methylpyrrolidin-2-yl)methanol was reacted with Pd/C (200 mg) for 18 hours with stirring under hydrogen atmosphere. Upon completion of the reaction, the mixture was filtered through a pad of diatomaceous earth and the filtrate was concentrated under reduced pressure and subsequently purified by silica gel column chromatography (eluent: 20% methanol/chloroform) to give a colorless liquid product (650 mg, 56% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 3.65 (dd, J = 10.0, 3.6 Hz, 1H), 3.43 (dd, J = 10.8, 2.0 Hz, 1H), 3.10-3.05 (m, 1H), 2.40-2.35 (m, 1H), 2.33 (s, 3H), 2.32-2.25 (m , 1H), 1.93-1.68 (m, 4H); mass spectrum (APCI+): m/z 116 [M + H]+.

50-00-0 Synthesis

50-00-0
893 suppliers
$10.00/25g

498-63-5
149 suppliers
$34.00/5g

3554-65-2
112 suppliers
$13.00/1g

Yield:3554-65-2 56%

Reaction Conditions:

with hydrogen;palladium 10% on activated carbon in water for 18 h;

Steps:

50.a
a) (/?S)-(1 -Methylpyrrolidin-2-yl)methanoIA mixture of (RS)-pyrrolidin-2-ylmethanol (1.00 g, 9.90 mrnol, 1.0 eq), formaldehyde (35% aqueous, 10 mL) and 10% Pd/C (200 mg) was stirred under a balloon of hydrogen gas for 18 h. The mixture was filtered through a Celite pad, concentrated under reduced pressure and purification by silica gel chromatography (20% MeOH/CHCI₃) gave a colorless liquid (650 mg, 56%); ¹H NMR (400 MHz, CDCI₃) 6 ppm 3.65 (dd, =10.0, 3.6 Hz, 1 H), 3.43 (dd, J=10.8, 2.0 Hz, 1H), 3.10-3.05 (m, 1 H), 2.40-2.35 (m, 1 H), 2.33 (s, 3H), 2.32-2.25 (m, 1 H), 1.93-1.68 (m, 4H); m/z (APCIf: 116 [M+H]⁺.

References:

MEDICAL RESEARCH COUNCIL TECHNOLOGY;OSBORNE, Simon;CHAPMAN, Timothy;WALLACE, Claire WO2012/127212, 2012, A1 Location in patent:Page/Page column 101

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933-94-8 Synthesis