tert-Butyl hydrogen (1,5-dihydroxypentan-2-yl)carbonimidate → (S)-tert-butyl tetrahydro-2H-pyran-3-ylcarbamate

HRID 246131Notes

Reaction equation

HRID 246131 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]([CH2:13][OH:14])[CH2:9][CH2:10][CH2:11]O)([CH3:4])([CH3:3])[CH3:2].C(C=P(CCCC)(CCCC)CCCC)#N>C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:9][CH2:10][CH2:11][O:14][CH2:13]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2734851tert-Butyl hydrogen (1,5-dihydroxypentan-2-yl)carbonimidateHCID 4622928Cyanomethylenetributylphosphorane

Product 1

HCID 67324694(S)-tert-butyl tetrahydro-2H-pyran-3-ylcarbamateYield 69.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
100 °C

Procedure

((S)-4-Hydroxy-1-hydroxymethyl-butyl)-carbamic acid tert-butyl ester (100 mg, 0.46 mmol) was dissolved in warm benzene (1.5 ml). Cyanomethylenetributylphosphorane (165 mg, 0.68 mmol) was added and the reaction vessel was sealed and stirred at 100° C. for 24 h. The reaction was cooled, evaporated and purified by silica gel chromatography (ethyl acetate/hexanes) to give 64 mg (69%) of (S)-(tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester. (M+Na)+=224.

Workup

  1. customthe reaction vessel was sealed
  2. temperatureThe reaction was cooled
  3. customevaporated
  4. custompurified by silica gel chromatography (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-8d75f19aab9b47eaa5c2d8c64266eecd
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…