Methyl propiolate → HCID 178500917, compound

HRID 1063626Notes

Reaction equation

HRID 1063626 reaction equation
[C:1]([O:5][C:6](=[O:16])[N:7]([C@H:9]1[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].C(P(CCCC)CCCC)CCC.[C:30]([O:34][CH3:35])(=[O:33])[C:31]#[CH:32]>C1COCC1>[CH3:35][O:34][C:30](=[O:33])[CH:31]=[CH:32][O:15][C@H:12]1[CH2:11][CH2:10][C@H:9]([N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:16])[CH3:8])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 13536Methyl propiolate2×HCID 13831Tributylphosphine2×HCID 178486055HCID 178486055, compound

Product 1

HCID 178500917HCID 178500917, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

27 g (117.7 mmol) of trans-(4-hydroxy-cyclohexyl)-methyl-carbamic acid tert-butyl ester were dissolved in 500 mL of THF and were treated with 6.8 mL of tri-n-butylphosphine and 10.5 mL (117.7 mmol) of methyl propiolate at 0° C. for 2d. Additional 2.1 mL (23 mmol, 0.2 eq) of methyl propiolate and 3.4 mL (11.8 mmol, 0.1 eq) of tri-n-butylphosphine were added. After stirring for 1 h at RT, the solution was evaporated and the crude product was purified by flash chromatography with n-heptane:EtOAc 3:1. Trituration with n-heptane yielded 26.7 g (73%) of trans-3-[4-(tert-butoxycarbonyl-methyl-amino)-cyclohexyloxy]-acrylic acid methyl ester as white solid, MS: 314 (MH+).

Workup

  1. customthe solution was evaporated
  2. customthe crude product was purified by flash chromatography with n-heptane:EtOAc 3:1

Sources & evidence

ORD record
ord-4e59b4b78f00462fa5e24d534a8d64aa
Source dataset
uspto-grants-2005_11
Patent number
US06965048B2

Reaction notes

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