Ethyl Acetate → HCID 58386793, compound

HRID 408471Notes

Reaction equation

HRID 408471 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:14][NH:13][CH2:12][C@H:11]([OH:15])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:16][CH2:17][O:18][C:19](C)=[O:20]>O1CCOCC1.O>[Si:1]([O:8][C@@H:9]1[CH2:10][C@@H:11]([OH:15])[CH2:12][N:13]([C:19]([O:18][CH2:17][C:16]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:14]=2)=[O:20])[CH2:14]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 21103800(3R,5R)-5-((tert-Butyldimethylsilyl)oxy)piperidin-3-ol

Product 1

HCID 58386793HCID 58386793, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of (3R,5R)-5-(tert-butyldimethylsilyloxy)piperidin-3-ol (1 eq) in 20 mL of 1,4-dioxane and 8 mL of water was added benzyl chloro formate (1.5 eq). The mixture was stirred at room temperature for 4 hours. The crude mixture was diluted with 100 mL of EtOAc, washed with brine, then dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc:hexanes=1:3) to yield (3R,5R)-benzyl 3-(tert-butyldimethylsilyloxy)-5-hydroxypiperidine-1-carboxylate (74%). LC/MS (m/z): 366.2 (MH+).

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash chromatography (EtOAc:hexanes=1:3)

Sources & evidence

ORD record
ord-4f15f5bcbc3a4fcf92b5fb71259243bf
Source dataset
uspto-grants-2014_06
Patent number
US08759338B2

Reaction notes

Loading…