Hydrochloric Acid → HCID 58386825, compound

HRID 73537Notes

Reaction equation

HRID 73537 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-f169acb65f814c96933d36670b29e4f6
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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