Benzyl Chloride → Methyl 3-(aminomethyl)-4-hydroxycyclopentane-1-carboxylate

To a stirred solution of (1SR,3SR,4RS)-3-cyano-4-hydroxy-cyclopentanecarboxylic acid methyl ester (185 mg) at r.t. in methanol (5 ml) under an argon atmosphere were added benzyl chloride (0.38 ml) and 10% Pd/C (50 mg). The mixture was stirred at r.t. under a hydrogen atmosphere (balloon) overnight. The catalyst was filtered off and washed with methanol. The filtrate was concentrated to leave a brown viscous oil. This was taken up in 10 ml sat. aq. NaHCO3 and extracted with CH2Cl2/MeOH 9:1 (3×10 ml) and CH2Cl2/MeOH 4:1 (10 ml). A white solid started to precipitate out of the biphasic mixture which was filtered off. The filtrate was neutralized by the addition of 1 N HCl and concentrated to leave crude (1SR,3SR,4RS)-3-aminomethyl-4-hydroxy-cyclopentane-carboxylic acid methyl ester as a light brown solid (189 mg).

1. filtrationThe catalyst was filtered off
2. washwashed with methanol
3. concentrationThe filtrate was concentrated
4. customto leave a brown viscous oil
5. extractionextracted with CH2Cl2/MeOH 9:1 (3×10 ml) and CH2Cl2/MeOH 4:1 (10 ml)
6. customto precipitate out of the biphasic mixture which
7. filtrationwas filtered off
8. additionThe filtrate was neutralized by the addition of 1 N HCl
9. concentrationconcentrated

ORD record

ord-9544c6b36b434cea8cb3fce49b6303d5

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678917B2