Ethyl propiolate → 3-Benzyl 2-tert-butyl (1R,3S,4S,6R)-6-{[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]oxy}-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate

HRID 456765Notes

Reaction equation

HRID 456765 reaction equation
[OH:1][C@H:2]1[C@H:7]2[CH2:8][C@H:4]([C@@H:5]([C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[N:6]2[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[C:26]([O:30][CH2:31][CH3:32])(=[O:29])[C:27]#[CH:28]>ClCCl>[CH2:31]([O:30][C:26](=[O:29])/[CH:27]=[CH:28]/[O:1][C@H:2]1[C@H:7]2[CH2:8][C@H:4]([C@@H:5]([C:16]([O:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[O:17])[N:6]2[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1)[CH3:32]

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 865989173-Benzyl 2-tert-butyl (1R,3S,4S,6R)-6-hydroxy-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate

Product 1

HCID 865989183-Benzyl 2-tert-butyl (1R,3S,4S,6R)-6-{[(1E)-3-ethoxy-3-oxo-1-propen-1-yl]oxy}-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-benzyl 2-tert-butyl (1R,3S,4S,6R)-6-hydroxy-2-azabicyclo[2.2.1]heptane-2,3-dicarboxylate obtained in Example 30-1 (593 mg) in dichloromethane (10 mL), were added ethyl propiolate (670 mg) and 4-methylmorphorine (190 mg). The mixture was stirred at room temperature for 3 hrs. The resulting mixture was evaporated in vacuo and the residue was chromatographed on silica gel eluting with hexane and ethyl acetate (4:1) to give the target compound (760 mg).

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. customthe residue was chromatographed on silica gel eluting with hexane and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-572a2243158d4904b7dd8b1627233535
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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