Methyl chloroformate → (R)-quinuclidin-3-yl 2-(methoxycarbonylamino)-2-phenylacetate

HRID 1619509Notes

Reaction equation

HRID 1619509 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:32])[O:30][CH3:31]>C(Cl)Cl>[CH3:31][O:30][C:29]([NH: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[CH2:12][CH2:11][N:10]([CH2:15][CH2:14]2)[CH2:9]1)=[O:6])=[O:32]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 67425463(R)-Quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride

Product 1

HCID 67607568(R)-quinuclidin-3-yl 2-(methoxycarbonylamino)-2-phenylacetateYield 40.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (R)-quinuclidin-3-yl 2-amino-2-phenylacetate dihydrochloride (I25) (150 mg, 0.45 mmol) in DCM (5 ml), were added triethylamine (188 μl, 1.35 mmol) and methyl carbonochloridate (41.7 μl, 0.54 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. The organic phase was dried over Na2SO4 and evaporated to obtain (R)-quinuclidin-3-yl 2-(methoxycarbonylamino)-2-phenylacetate (58.0 mg; 40% yield). The compound 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 materialThe organic phase was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-b57e3d1877d346b2bc54c2fe27955ffa
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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