HCID 13539135, compound → HCID 54288325, compound

To a suspension of 3.8 gm (100 mMol) lithium aluminum hydride in 200 mL tetrahydrofuran were added dropwise a solution of 10.0 gm (50.0 mMol) 1-methyl-cis-3,4-pyrrolidinedicarboxylic acid dimethyl ester in 50.0 mL tetrahydrofuran. The reaction mixture was stirred at ambient for about 1 hour and was then quenched by the sequential addition of 3.8 mL water, 3.8 mL 15% aqueous sodium hydroxide solution and 11.4 mL of water. The resultant mixture was stirred at ambient for 20 hours. At this point the suspension was filtered through a bed of Celite and the filter cake was washed with tetrahydrofuran. The combined liltrates were concentrated in vacuo to give 6.7 gm of the desired compound as a light yellow oil.

1. customwas then quenched by the sequential addition of 3.8 mL water, 3.8 mL 15% aqueous sodium hydroxide solution and 11.4 mL of water
2. stirringThe resultant mixture was stirred at ambient for 20 hours
3. filtrationAt this point the suspension was filtered through a bed of Celite
4. washthe filter cake was washed with tetrahydrofuran
5. concentrationThe combined liltrates were concentrated in vacuo

ORD record

ord-55f23a8e39284ec1954f0d8b5e192300

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05457121