Acetonitrile--water (1/1) → HCID 117843852, compound

HRID 1480987Notes

Reaction equation

HRID 1480987 reaction equation
[C:1]([O:5][C:6]([C:8]1([C:14]#[N:15])[CH2:13][CH2:12][S:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC#N.[OH2:19]>CCOC(C)=O>[C:1]([O:5][C:6]([C:8]1([C:14]#[N:15])[CH2:13][CH2:12][S:11](=[O:19])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 18373917Acetonitrile--water (1/1)HCID 89812942HCID 89812942, compound

Product 1

HCID 117843852HCID 117843852, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-cyano-tetrahydro-thiopyran-4-carboxylic acid tert-butyl ester (206 mg) and NaIO4 (217 mg) in MeCN/water (3 mL/3 mL) was stirred between 0° C. and rt overnight; then the reaction was diluted with EtOAc, washed with dil. Na2SO3 solution, water and dil. NaCl solution respectively; EtOAc phase was dried over anhydrous sodium sulphate, filtered, concentrated and column-purified to give the desired product (193 mg). 1H NMR in CDCl3, δ in ppm: 3.2-2.6 (m, 6H), 2.4-2.1 (m, 2H), and 1.52 (s, 9H).

Workup

  1. washwashed with dil. Na2SO3 solution, water and dil. NaCl solution respectively
  2. dry with materialEtOAc phase was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customcolumn-purified

Sources & evidence

ORD record
ord-c3c803fee25e40ee83da922c5cb13b56
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

Loading…