Reaction #53922

ord-3be0d935e22a48a8b35edee8c35950cd

Reaction equation

CN(C(=O)OC(C)(C)C)[C@H]1CC[C@H](C#CCCOC2CCCCO2)CC1
trans-Methyl-{4-[4-(tetrahydro-pyran-2-yloxy)-but-1-ynyl]-cyclohexyl}-carbamic acid tert-butyl ester
Cc1ccc(S(=O)(=O)[O-])cc1
toluene-4-sulfonate
→
CN(C(=O)OC(C)(C)C)[C@H]1CC[C@H](C#CCCO)CC1
trans-[4-(4-Hydroxy-but-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester
Yield 107.3%

Reactants

CN(C(=O)OC(C)(C)C)[C@H]1CC[C@H](C#CCCOC2CCCCO2)CC1
trans-Methyl-{4-[4-(tetrahydro-pyran-2-yloxy)-but-1-ynyl]-cyclohexyl}-carbamic acid tert-butyl ester
Cc1ccc(S(=O)(=O)[O-])cc1
toluene-4-sulfonate

Reagents

None

Solvents

CO
MeOH

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe reaction was partitioned between aqueous solution of 10% KHSO4/ether (3×)
  2. 2
    WashThe organic phases were washed with aqueous saturated NaHCO3, 10% NaCl
  3. 3
    Dryingdried over Na2SO4
  4. 4
    Otherevaporated

Procedure

A solution of 3.45 g (9.44 mmol) of trans-Methyl-{4-[4-(tetrahydro-pyran-2-yloxy)-but-1-ynyl]-cyclohexyl}-carbamic acid tert-butyl ester and 0.7 g (2.83 mmol) of pyrimidium toluene-4-sulfonate in 25 ml MeOH was stirred at 55° C. for 1.5 h. The reaction was partitioned between aqueous solution of 10% KHSO4/ether (3×). The organic phases were washed with aqueous saturated NaHCO3, 10% NaCl, dried over Na2SO4 and evaporated to give 2.85 g (quantitative) of trans-[4-(4-Hydroxy-but-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester, MS: 281 (M).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858651B2uspto-grants-2005_02