Triethylamine → (R)-quinuclidin-3-yl 2-phenyl-2-(vinyloxycarbonylamino)acetate

HRID 1619516Notes

Reaction equation

HRID 1619516 reaction equation
Cl.Cl.[NH2:3][CH:4]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:5]([O:7][C@@H:8]1[CH:13]2[CH2:14][CH2:15][N:10]([CH2:11][CH2:12]2)[CH2:9]1)=[O:6].C(N(CC)CC)C.[C:29](Cl)(=[O:33])[O:30][CH:31]=[CH2:32]>C(Cl)Cl>[C:16]1([CH:4]([NH:3][C:29]([O:30][CH:31]=[CH2:32])=[O:33])[C:5]([O:7][C@@H:8]2[CH:13]3[CH2:12][CH2:11][N:10]([CH2:15][CH2:14]3)[CH2:9]2)=[O:6])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78808Vinyl chloroformateHCID 67425463(R)-Quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride

Product 1

HCID 67605833(R)-quinuclidin-3-yl 2-phenyl-2-(vinyloxycarbonylamino)acetateYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (R)-quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride (I25) (110 mg, 0.33 mmol) in DCM (5 ml), were added triethylamine (138 μl, 0.99 mmol) and vinyl carbonochloridate (36.2 μl, 0.40 mmol). The reaction was stirred at RT for 4 hours, and then the solvent was evaporated. The residue was taken up with EtOAc and washed with water and brine, dried over Na2SO4 and evaporated to dryness to obtain (R)-quinuclidin-3-yl 2-phenyl-2-(vinyloxycarbonylamino)acetate (70 mg; 64% yield). The product was used in the next step without any further purification.

Workup

  1. customthe solvent was evaporated
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-e2096a44270f4a7c92a05cfd6d276258
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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