Ammonium Chloride → HCID 66959152, compound

HRID 1244460Notes

Reaction equation

HRID 1244460 reaction equation
[CH:1]1([Mg]Cl)[CH2:5][CH2:4][CH2:3][CH2:2]1.[N:8]12[CH2:15][CH2:14][CH:11]([CH2:12][CH2:13]1)[C@@H:10]([O:16][C:17](=[O:25])[C:18]([C:20]1[O:21][CH:22]=[CH:23][CH:24]=1)=[O:19])[CH2:9]2.[Cl-].[NH4+]>CCOCC.C1COCC1>[N:8]12[CH2:15][CH2:14][CH:11]([CH2:12][CH2:13]1)[C@@H:10]([O:16][C:17](=[O:25])[C:18]([CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)([C:20]1[O:21][CH:22]=[CH:23][CH:24]=1)[OH:19])[CH2:9]2

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 665920532-fur-2-yl-2-oxoacetic acid (3R)-1-azabicyclo[2.2.2]oct-3-yl esterHCID 178478989HCID 178478989, compound

Product 1

HCID 66959152HCID 66959152, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Cyclopentylmagnesium cloride, 0.0472 mol (23.6 ml of a solution 2M in ether) was added to a solution of 9.4 g (0.0377 mol) of 2-fur-2-yl-2-oxoacetic acid (3R)-1-azabicyclo[2.2.2]oct-3-yl ester dissolved in 125 ml of THF, at −70° C. under a N2 atmosphere. The mixture was stirred at this temperature for 10 minutes, and then warmed to room temperature. After 16 h, the reaction mixture was treated with a saturated solution of ammonium chloride and extracted twice with ethyl acetate. The organic phases were combined, washed with water, and dried over MgSO4. After removal of the solvent, the oil obtained (7.5 g) was purified by chromatography on silica gel eluting with chloroform/methanol/ammonia 95:5:0.5. Appropiate fractions were combined and evaporated to obtain the two diastereomers: I-14a, I-14b

Workup

  1. waitAfter 16 h
  2. extractionextracted twice with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. customAfter removal of the solvent
  6. customthe oil obtained (7.5 g)
  7. customwas purified by chromatography on silica gel eluting with chloroform/methanol/ammonia 95:5:0.5
  8. customevaporated
  9. customto obtain the two diastereomers

Sources & evidence

ORD record
ord-fb9b32a06f17480ab1937261aee3593a
Source dataset
uspto-grants-2006_10
Patent number
US07122558B2

Reaction notes

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