N-Ethylpiperidine → HCID 67791575, compound

HRID 1650300Notes

Reaction equation

HRID 1650300 reaction equation
C(O[C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH3:11])(=O)C.C(N1CCCCC1)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[CH2:40]([O:43][C:44]([N:46]1[CH2:50][C@H:49]([O:51][C:52](=[O:55])[NH:53][CH3:54])[CH2:48][C@H:47]1[CH:56]=[C:57]([CH3:61])[C:58](=[O:60])[CH3:59])=[O:45])[CH:41]=[CH2:42].C(=O)([O-])O.[Na+]>ClCCl.O.C(OCC)(=O)C>[CH2:40]([O:43][C:44]([N:46]1[CH2:50][C@H:49]([O:51][C:52](=[O:55])[NH:53][CH3:54])[CH2:48][C@H:47]1[CH:56]=[C:57]([CH3:61])[C:58](=[O:60])[CH2:59][C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][Si:13]([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:14])[CH3:15])[CH3:11])=[O:45])[CH:41]=[CH2:42]

Participants

9

Reactant 5

HCID 13007N-Ethylpiperidine2×HCID 65367Trimethylsilyl triflate2×HCID 516892Sodium BicarbonateHCID 10935078AzetidonHCID 57063098HCID 57063098, compound

Product 1

HCID 67791575HCID 67791575, compoundYield 72.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (3R,4R)-4-acetoxy-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (1.48 g) and N-ethylpiperidine (0.69 ml) in dichloromethane (10 ml) was added trimethylsilyl trifluoromethanesulfonate (1.0 ml) at -20° C., and the resulting mixture was stirred at 0° C. for 1 hour (Solution A). To a solution of (2S,4R)-1-allyloxycarbonyl-4-(methylcarbamoyloxy)-2-(2-methyl-3-oxo-1-butenyl)pyrrolidine (1.60 g) and N-ethylpiperidine (1.50 ml) in dichloromethane (20 ml) was added trimethylsilyl trifluoromethanesulfonate (2.5 ml) at -20° C. and the resulting mixture was stirred at 0° C. for 1 hour. To this mixture was added dropwise the above obtained Solution A at 0° C. and the resulting mixture was stirred for another 1 hour at 0° C. The resulting mixture was taken up into a mixture of ethyl acetate (150 ml) and water (150 ml) and the mixture was stirred at ambient temperature for 2 hours. After adjusting pH to around 6.5 with aqueous sodium hydrogen carbonate, the organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (75 ml) eluting with a mixture of n-hexane and ethyl acetate (7:3-0:10 V/V) to give (3S,4R)-4-[4-{(2S,4R)-1-allyloxycarbonyl-4-(methylcarbamoyloxy)pyrrolidin-2-yl}-3-methyl-2-oxo-3-butenyl]-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-2-oxoazetidine (2.00 g).

Workup

  1. stirringthe resulting mixture was stirred for another 1 hour at 0° C
  2. stirringthe mixture was stirred at ambient temperature for 2 hours
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica gel (75 ml)
  8. washeluting with a mixture of n-hexane and ethyl acetate (7:3-0:10 V/V)

Sources & evidence

ORD record
ord-cfef4e6b4f8d41b2a46bd27397382ae9
Source dataset
uspto-grants-1990_05
Patent number
US04923857

Reaction notes

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