Heptane → (2R)-tert-butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate

HRID 406496Notes

Reaction equation

HRID 406496 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C@H:27]1[CH2:31][N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@H:29]([CH3:39])[CH2:28]1)(C(C)(C)C)(C)C.CCCCCCC>C1COCC1>[OH:26][CH:27]1[CH2:31][N:30]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C@H:29]([CH3:39])[CH2:28]1

Participants

5

Reactant 3

HCID 8900HeptaneHCID 2724141Tetrabutylammonium FluorideHCID 10979991HCID 10979991, compound

Product 1

HCID 58470941(2R)-tert-butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylateYield 92.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tetrabutylammonium fluoride (1M in THF, 28 mL) was added to a solution of (2R,4R)-tert-butyl 4-(tert-butyldimethylsilyloxy)-2-methylpyrrolidine-1-carboxylate (3.87 g, 12.27 mmol) in THF (10 mL). The reaction mixture was stirred at ambient temperature for about 3 hours. The solvent was removed in vacuo and the residue partitioned between EtOAc and water. The aqueous phase was further extracted with EtOAc (3×100 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel flash chromatography eluting with 40% EtOAc:heptane yielded (2R)-tert-butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate (2.3 g, 11.4 mmol) as a colorless oil. 1H NMR (d6 DMSO, 400 MHz) 4.41 (1H, br), 4.00 (1H, br), 3.48 (2H, br), 2.3-2.0 (2H, m), 1.72 (1H, m), 1.46 (9H, s) and 1.22 (3H, d).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between EtOAc and water
  3. extractionThe aqueous phase was further extracted with EtOAc (3×100 mL)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by silica gel flash chromatography
  8. washeluting with 40% EtOAc

Sources & evidence

ORD record
ord-95cf7d854af646e3aec3c05a0b54c9dd
Source dataset
uspto-grants-2014_06
Patent number
US08754107B2

Reaction notes

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