Dicyclohexylcarbodiimide → HCID 86688909, compound

HRID 404651Notes

Reaction equation

HRID 404651 reaction equation
[C:1]([CH:4]1[CH2:9][CH2:8][N:7]([CH:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]([OH:13])=[O:12])[CH2:6][CH2:5]1)(=[O:3])[NH2:2].C1CCC(N=C=NC2CCCCC2)CC1.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:1]([CH:4]1[CH2:9][CH2:8][N:7]([CH:10]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:11]([O:13][C@@H:47]2[CH:48]3[CH2:51][CH2:52][N:45]([CH2:50][CH2:49]3)[CH2:46]2)=[O:12])[CH2:6][CH2:5]1)(=[O:3])[NH2:2]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 20988035HCID 20988035, compound

Product 1

HCID 86688909HCID 86688909, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Carbamoylpiperidin-1-yl)-2-phenylacetic acid (145 mg, 0.55 mmol) was suspended in dry THF (5.5 ml) and DCC (240 mg, 1.16 mmol), HOBT (157 mg, 1.16 mmol) and (R)-quinuclidin-3-ol (148 mg, 1.16 mmol) were sequentially added. The mixture was stirred at room temperature under nitrogen atmosphere for 24 hours. The white solid was filtered off and the solution was evaporated. The crude was purified by flash chromatography (DCM/MeOH/NH4OH=95/5/0.5) to obtain (R)-quinuclidin-3-yl 2-(4-carbamoylpiperidin-1-yl)-2-phenylacetate (78 mg, 38% yield) as an off-white spongy solid.

Workup

  1. filtrationThe white solid was filtered off
  2. customthe solution was evaporated
  3. customThe crude was purified by flash chromatography (DCM/MeOH/NH4OH=95/5/0.5)

Sources & evidence

ORD record
ord-d54d7f24846f46d8968e3d2cb9239646
Source dataset
uspto-grants-2014_06
Patent number
US08748613B2

Reaction notes

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