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

HRID 1662718
Notes
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Reaction equation

HRID 1662718 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 67430579tert-butyl (2S,4R)-2-[(dimethylamino)carbonyl]-4-(2-ethoxy-2-oxo ethoxy)pyrrolidine-1-carboxylate

Product 1

HCID 67430889tert-butyl (2S,4R)-2-[(dimethylamino)carbonyl]-4-(2-hydroxyethoxy)pyrrolidine-1-carboxylateYield 115%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

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

  1. stirringthe reaction mixture was stirred at room temperature for one hour
  2. filtrationThe insoluble matter was filtered with celite
  3. 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

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes