Water → HCID 86617980, compound

HRID 1446334Notes

Reaction equation

HRID 1446334 reaction equation
[CH:1]([C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:2].[C:15]1([Mg]Br)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+].O>C1COCC1.C(OCC)(=O)C>[OH:2][CH:1]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 7009153N-(tert-Butoxycarbonyl)-D-prolinalHCID 178418255HCID 178418255, compound

Product 1

HCID 86617980HCID 86617980, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (2R)-2-formylpyrrolidine-1-carboxylate (500 mg, 2.51 mmol) in dry THF (7 mL) at −78° C. was added 1 M phenylmagnesium bromide solution in THF (7.5 mL, 7.5 mmol, 3 eq.). After stirring the reaction mixture for 2 h, saturated aqueous ammonium chloride (1.5 mL) was added. The mixture was warmed to room temperature, and water (50 mL) and ethyl acetate (25 mL) were added. The phases were separated, and the aqueous layer was extracted with ethyl acetate (25 mL). The combined organic phases were washed with 10% citric acid, brine, saturated aqueous sodium bicarbonate, and dried over MgSO4. The solvent was evaporated and the residue was purified by silica gel chromatography (pentane/ethyl acetate, 7:3) to give tert-butyl (2R)-2-[hydroxy(phenyl)methyl]pyrrolidine-1-carboxylate a colorless oil. Subsequent BOC deprotection was carried out by dissolving the intermediate in ethyl acetate (3 mL) and leading a stream of HCl (g) through the solution for 20 min. The solvent was evaporated to give the title compound as a colorless oil.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (25 mL)
  3. washThe combined organic phases were washed with 10% citric acid, brine, saturated aqueous sodium bicarbonate
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated
  6. customthe residue was purified by silica gel chromatography (pentane/ethyl acetate, 7:3)

Sources & evidence

ORD record
ord-85bd5574b65f449482f04f756461fe60
Source dataset
uspto-grants-2010_02
Patent number
US07666888B2

Reaction notes

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