Water → (R)-3-hydroxy-1-phenylpyrrolidin-2-one

HRID 1098675Notes

Reaction equation

HRID 1098675 reaction equation
[Si]([O:18][C@@H:19]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:20]1=[O:30])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[OH:18][C@@H:19]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:20]1=[O:30]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 59593433HCID 59593433, compound

Product 1

HCID 59593452(R)-3-hydroxy-1-phenylpyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3R)-3-(tert-butyldiphenylsilyloxy)-1-phenylpyrrolidin-2-one (2.88 g, 6.93 mmol) in THF (8.6 mL) at 0° C. was added TBAF (13.9 mL of 1 M in THF, 13.86 mmol) slowly and the reaction mixture was stirred at RT for 3 h. The reaction mixture was poured into water and extracted with EtOAc (3×). The combined organics were dried over Na2SO4 and evaporated to dryness. Purification by silica gel chromatography (0-10% MeOH in DCM) gave (R)-3-hydroxy-1-phenylpyrrolidin-2-one as a white solid (0.9 g 73%). 1H-NMR (400 MHz, DMSO-d6) δ 7.69 (d, J=7.8 Hz, 2H), 7.40-7.36 (m, 2H), 7.14 (t, J=7.4 Hz, 1H), 5.75 (d, J=5.8 Hz, 1H), 4.33-4.27 (m, 1H), 3.77-3.66 (m, 2H), 2.44-2.36 (m, 1H) and 1.86-1.81 (m, 1H) ppm.

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined organics were dried over Na2SO4
  3. customevaporated to dryness
  4. customPurification by silica gel chromatography (0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-21359f7c4648460faaa7358b3626b56c
Source dataset
uspto-grants-2012_03
Patent number
US08143297B2

Reaction notes

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