Sodium sulfate decahydrate → tert-butyl (2S,4R)-2-[(dimethylamino)carbonyl]-4-(2-hydroxyethoxy)pyrrolidine-1-carboxylate

HRID 1662718Notes

Reaction equation

[CH3:1][N:2]([CH3:24])[C:3]([C@@H:5]1[CH2:9][C@@H:8]([O:10][CH2:11][C:12](OCC)=[O:13])[CH2:7][N:6]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:4].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:1][N:2]([CH3:24])[C:3]([C@@H:5]1[CH2:9][C@@H:8]([O:10][CH2:11][CH2:12][OH:13])[CH2:7][N:6]1[C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])=[O:4]

Participants

Conditions

Temperature: -10 °C

Procedure

Under nitrogen atmosphere, to a solution of 2.00 g of the compound obtained in Step 143-1 in THF (40 ml) was added 360 mg of LAH at −40° C., and the reaction mixture was stirred at −10° C. for one hour. To the solution was added sodium sulfate 10 hydrate and the reaction mixture was stirred at room temperature for one hour. The insoluble matter was filtered with celite, the solvent was evaporated under reduced pressure to obtain 2.02 g of the title compound.

Workup

stirringthe reaction mixture was stirred at room temperature for one hour
filtrationThe insoluble matter was filtered with celite
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-45d5fdd74d344f7bbe57cbdfb0509a36
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030499B2

Reaction notes

Loading…