Methyl N-(triethylammoniosulfonyl)carbamate → HCID 86627343, compound

HRID 1896005Notes

Reaction equation

HRID 1896005 reaction equation
O[C:2]([CH:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)([CH3:11])[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>O>[CH2:11]=[C:2]([CH:12]1[CH2:13][CH2:14][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:16][CH2:17]1)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 68725969tert-Butyl 4-(1-hydroxy-1-methyl-3-phenylprop-2-ynyl)piperidine-1-carboxylate

Product 1

HCID 86627343HCID 86627343, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A well homogenised mixture of Compound 253a (0.3 g, 0.911 mmol) and Burgess' reagent (Methyl N-(triethylammoniumsulphonyl)carbamate) (0.35 g, 1.49 mmol) was heated at 60° C. for 2 h. Afterwards, the reaction mixture was cooled, poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with Petroleum Ether-EtOAc 95:5, affording the title products as an oily mixture.

Workup

  1. temperatureAfterwards, the reaction mixture was cooled
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. customdried on Na2SO4
  5. customevaporated to dryness in vacuo
  6. customto afford a residue, which
  7. customwas purified by automated flash liquid chromatography (Horizon™-Biotage)
  8. washeluting with Petroleum Ether-EtOAc 95:5

Sources & evidence

ORD record
ord-1fd8cc4a088f4435bc0dd65216694949
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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