Potassium tert-butoxide → HCID 22875342, compound

HRID 2256087Notes

Reaction equation

HRID 2256087 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([OH:13])[C@H:10]([NH:14][C@@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23][C:24](C)([O-:26])C.[K+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]2[C@H:10]([N:14]([C@@H:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH3:16])[C:24](=[O:26])[CH2:23][O:13]2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 69950762HCID 69950762, compound

Product 1

HCID 22875342HCID 22875342, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.14 g of trans-1-tert-butoxycarbonyl -4-hydroxy-3-[(1R)-1-phenylethylamino]pyrrolidine 8a in 200 of tetrahydrofuran was added 1 g of potassium tert-butoxide. The mixture was stirred at room temperature for 20 minutes. The solvent was removed under reduced pressure and a residue was subjected to silica gel column chromatography. From an eluant of a mixture of hexane and ethyl acetate (1:1 by volume), the titled compound 9a weighing 2.45 g was obtained as an oil.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionFrom an eluant of a mixture of hexane and ethyl acetate (1:1 by volume)
  3. customwas obtained as an oil

Sources & evidence

ORD record
ord-9173b772e891425ab11231c5c9615b8d
Source dataset
uspto-grants-1997_08
Patent number
US05654318

Reaction notes

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