Ozone → [(2R,3R)-2-formyl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

HRID 1169231Notes

Reaction equation

HRID 1169231 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][O:10][C@@H:9]1[CH:14]=CC1C=CC=CC=1)([CH3:4])([CH3:3])[CH3:2].[O:23]=[O+][O-]>CO>[C:1]([O:5][C:6](=[O:22])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][O:10][C@H:9]1[CH:14]=[O:23])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 24823OzoneHCID 69748163[(2r,3r)-2-Styryl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 59094967[(2R,3R)-2-formyl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl esterYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
23 °C

Procedure

Through a stirring solution of [(2R,3R)-2-styryl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester (27 mg, 0.089 mmol) in methanol (2 mL) at −78° C. was bubbled ozone until the reaction solution was blue in color. Excess triphenylphosine (500 mg) was added, and the reaction was allowed to warm to 23° C. The resulting mixture was concentrated and purified by flash chromatography (SiO2, 7-40% ethyl acetate in hexanes) to give the desired aldehyde (20 mg, 98%) as a pale yellow oil. MS (APCI), m+/z: (M+H)+=230.

Workup

  1. additionExcess triphenylphosine (500 mg) was added
  2. concentrationThe resulting mixture was concentrated
  3. custompurified by flash chromatography (SiO2, 7-40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f074a9ab2c54412da5bb2d2fc70c9faa
Source dataset
uspto-grants-2003_09
Patent number
US06627629B2

Reaction notes

Loading…