p-Toluenesulfonate → HCID 69784823, compound

HRID 1063374Notes

Reaction equation

HRID 1063374 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[C:15][CH2:16][CH2:17][O:18]C2CCCCO2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S([O-])(=O)=O)=CC=1>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[C:15][CH2:16][CH2:17][OH:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 85570p-ToluenesulfonateHCID 69784474HCID 69784474, compound

Product 1

HCID 69784823HCID 69784823, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4.5 g (13.4 mmol) of 4-[4-(Tetrahydro-pyran-2-yloxy)-but-1-ynyl]-piperidine-1-carboxylic acid tert-butyl ester and 1 g (4mmol) of pyrimidium toluene-4-sulfonate in 45 ml MeOH was stirred at 55° C. for 1 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 3.26 g (97%) of 4-(4-Hydroxy-but-1-ynyl)-piperidine-1-carboxylic acid tert-butyl ester, MS: 254 (MH+).

Workup

  1. customThe reaction was partitioned between aqueous solution of 10% KHSO4 /ether (3×)
  2. washThe organic phases were washed with aqueous saturated NaHCO3, 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-9b745ab9b64942428efec91c565fffa1
Source dataset
uspto-grants-2005_11
Patent number
US06964974B2

Reaction notes

Loading…