Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-phenyl-2-(o-tolylamino)acetate

HRID 1044048Notes

Reaction equation

HRID 1044048 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.Cl.[C:17]1([CH:23]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[C:24]([OH:26])=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1C=CC2N(O)N=NC=2C=1.[N:45]12[CH2:52][CH2:51][CH:48]([CH2:49][CH2:50]1)[C@@H:47](O)[CH2:46]2>C1COCC1>[C:17]1([CH:23]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[CH3:34])[C:24]([O:26][C@@H:47]2[CH:48]3[CH2:51][CH2:52][N:45]([CH2:50][CH2:49]3)[CH2:46]2)=[O:25])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 67124826Phenyl-o-methylphenylamino-acetic acid hydrochloride

Product 1

HCID 46840573(R)-quinuclidin-3-yl 2-phenyl-2-(o-tolylamino)acetateYield 103%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

PS-DCC (1.15 g, 1.44 mmol, loading: 1.25 mmol/g) was suspended in THF (15 ml). 2-Phenyl-2-(o-tolylamino)acetic acid hydrochloride (I22) (200 mg, 0.72 mmol) and HOBT (221 mg, 1.44 mmol) were added, followed by (R)-quinuclidin-3-ol (275 mg, 2.16 mmol), and the mixture was stirred for 16 hours at room temperature. PS-DCC was removed by filtration, and the filtrate was evaporated. The resulting residue was dissolved in EtOAc and washed sequentially with water, sat. NaHCO3, water and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give the title compound (260 mg, quantitative yield, mixture of diastereomers).

Workup

  1. customPS-DCC was removed by filtration
  2. customthe filtrate was evaporated
  3. dissolutionThe resulting residue was dissolved in EtOAc
  4. washwashed sequentially with water, sat. NaHCO3, water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d70e26e257bd4bc6922ebf2e9eb74833
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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