Ammonium fluoride → HCID 54216103, compound

HRID 323435Notes

Reaction equation

HRID 323435 reaction equation
[CH3:1][C@@H:2]([N:9]1[CH2:13][CH2:12][C:11]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)([CH2:14][CH2:15][O:16][Si](C(C)(C)C)(C)C)[C:10]1=[O:32])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F-].[NH4+]>>[CH3:1][C@@H:2]([N:9]1[CH2:13][CH2:12][C:11]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)([CH2:14][CH2:15][OH:16])[C:10]1=[O:32])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 25516Ammonium fluorideHCID 54444546HCID 54444546, compound

Product 1

HCID 54216103HCID 54216103, compound

Procedure

Prepare by the method of Example 18.2 using 1-((R)-α-methylbenzyl)-3-(4-fluorophenylmethyl)-3-(2-(t-butyldimethylsilyloxy)ethyl)-2-oxopyrrolidine (1.7 g, 3.73 mmol) and ammonium fluoride (0.83 g, 22.4 mmol) to give, after chromatography on silica gel eluted with 1/1 ethyl acetate/hexane, the title compound as diastereomers: Rf=0.51 and 0.25 (silica gel, 1/1 ethyl acetate/hexane).

Workup

  1. customto give
  2. washafter chromatography on silica gel eluted with 1/1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-daee0064fe18432ca51680fc0239d92b
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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