Triacetoxyperiodinane → HCID 131733581, compound

HRID 1749447Notes

Reaction equation

HRID 1749447 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][C:3]1([CH3:17])[CH3:16].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:16][C:3]1([CH3:17])[C:2](=[O:1])[CH2:7][CH2:6][C@@H:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 131733582HCID 131733582, compound

Product 1

HCID 131733581HCID 131733581, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl ((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)carbamate (2 g crude) in DCM (110 mL) was added Dess-Martin periodinane (4.24 g, 10 mmol) keeping the temperature below 5° C. The resulting mixture was stirred at room temperature for 1 h. The reaction was diluted with DCM and washed with saturated solution of sodium bicarbonate. The separated organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by silica gel chromatography column (6% ethyl acetate in petroleum ether) to afford the title compound as a yellow oil (1.10 g, 4.56 mmol, 65% yield over two steps). MS (ESI) m/z 242.2 [M+H]+.

Workup

  1. customthe temperature below 5° C
  2. washwashed with saturated solution of sodium bicarbonate
  3. dry with materialThe separated organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe filtrate was evaporated under reduced pressure
  6. customthe residue was purified by silica gel chromatography column (6% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-679244fc7fc242b09bc469e1bed2ae62
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

Loading…