D-Tartaric acid → HCID 10264161, compound

1,200 ml of a 60% aqueous solution of acetic acid was added to 125.5 g of (3R*,4S*,5R*)-1-benzyl-3,4-bis(tert-butyldimethylsilyloxy)-5-(2-hydroxyethyl)-2-pyrrolidinone which had been prepared according to the procedure described in J. Org. Chem. 60, 103-108 (1995) by using D-tartaric acid as the starting material. After this mixture was refluxed overnight and concentrated under reduced pressure, 300 ml of concentrated aqueous ammonia and 500 ml of methanol were added to the resulting residue, followed by stirring at room temperature overnight. After the reaction mixture was concentrated under reduced pressure, the resulting residue was purified by silica gel column chromatography (using a 10:1 mixture of chloroform and methanol as the eluent) to obtain 35 g of (3R*,4S*,5R*)-1-benzyl-3,4-dihydroxy-5-(2-hydroxyethyl)-2-pyrrolidinone.

1. customhad been prepared
2. temperatureAfter this mixture was refluxed overnight
3. concentrationconcentrated under reduced pressure, 300 ml of concentrated aqueous ammonia and 500 ml of methanol
4. additionwere added to the resulting residue
5. concentrationAfter the reaction mixture was concentrated under reduced pressure
6. customthe resulting residue was purified by silica gel column chromatography (
7. additiona 10:1 mixture of chloroform and methanol as the eluent)

ORD record

ord-703b3fd8b8844b4182e78f4c80df698b

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017911