Hydrochloric Acid → HCID 58386825, compound

HRID 408473Notes

Reaction equation

HRID 408473 reaction equation
[Si]([O:8][C@@H:9]1[CH2:14][C@@H:13]([O:15][CH3:16])[CH2:12][N:11]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:10]1)(C(C)(C)C)(C)C.Cl.C(O)(C)C>CO>[OH:8][C@@H:9]1[CH2:14][C@@H:13]([O:15][CH3:16])[CH2:12][N:11]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 58386789HCID 58386789, compound

Product 1

HCID 58386825HCID 58386825, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3R,5R)-benzyl 3-(tert-butyldimethylsilyloxy)-5-methoxypiperidine-1-carboxylate (1 eq) in 30 mL of methanol was added 3.8M HCl in isopropanol (4 eq). The reaction mixture was allowed to stand at room temperature for 3 hours at which point it was concentrated under reduced pressure. The resulting residue was diluted with 100 mL of EtOAc, washed with sat. aq. sodium bicarbonate, brine, then dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (EtOAc:hexanes=2:1) to yield (3R,5R)-benzyl 3-hydroxy-5-methoxypiperidine-1-carboxylate (92%). LC/MS (m/z): 266.2 (MH+).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionThe resulting residue was diluted with 100 mL of EtOAc
  3. washwashed with sat. aq. sodium bicarbonate, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography (EtOAc:hexanes=2:1)

Sources & evidence

ORD record
ord-5db02698030f4df1ad739b1daf52fe98
Source dataset
uspto-grants-2014_06
Patent number
US08759338B2

Reaction notes

Loading…