Sodium Sulfate → tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 1292682Notes

Reaction equation

HRID 1292682 reaction equation
C[O:2][C:3](=O)[C@@H:4]1[CH2:8][C@@H:7]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH2:6][N:5]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1.CCOC(C)=O>[C:20]([O:19][C:17]([N:5]1[CH2:6][C@H:7]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH2:8][C@H:4]1[CH2:3][OH:2])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 62649Sodium sulfate decahydrateHCID 10618477(2S,4R)-1-tert-Butyl 2-methyl 4-((tert-butyldimethylsilyl)oxy)pyrrolidine-1,2-dicarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11078078tert-butyl (2S,4R)-4-((tert-butyldimethylsilyl)oxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of N-t-butoxycarbonyl-4-(R)-t-butyldimethylsilyloxy proline methyl ester (86.65 g, 241 mmol), in THF (150 ml), was added over 90 minutes to a solution of lithium aluminum hydride (247 ml of a 1M solution in THF, 247 mmol), under argon, so that the temperature did not exceed 12° C. Stirring was continued for 50 mins and then EtOAc (500 ml) was added cautiously, followed by sodium sulphate decahydrate (34 g), and the resulting mixture stirred for 16 hrs at room temperature. Anhydrous sodium sulphate (34 g) was added and the mixture stirred an additional 30 min and then filtered. The solids were washed with EtOAc (800 ml), the filtrates combined and the solvent evaporated in vacuo. The title compound was obtained as a colourless oil and used in the next step without further purification.

Workup

  1. customdid not exceed 12° C
  2. stirringthe resulting mixture stirred for 16 hrs at room temperature
  3. stirringthe mixture stirred an additional 30 min
  4. filtrationfiltered
  5. washThe solids were washed with EtOAc (800 ml)
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-144a94185d274b0a820d22d283f2a01a
Source dataset
uspto-grants-1998_05
Patent number
US05756528

Reaction notes

Loading…