Hydrochloric Acid → HCID 59455752, compound

HRID 1920163Notes

Reaction equation

HRID 1920163 reaction equation
[C:1]([O:9][C@H:10]1[CH2:15][C@@H:14]([O:16][Si](C(C)(C)C)(C)C)[CH2:13][N:12]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(O)(C)C>CO>[C:1]([O:9][C@H:10]1[CH2:15][C@@H:14]([OH:16])[CH2:13][N:12]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 59455633HCID 59455633, compound

Product 1

HCID 59455752HCID 59455752, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3S,5R)-benzyl 3-(benzoyloxy)-5-(tert-butyl-dimethylsilyloxy)-piperidine-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 120 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=1:1) to yield (3S,5R)-benzyl 3-(benzoyloxy)-5-hydroxypiperidine-1-carboxylate (95%). LC/MS (m/z): 355.9 (MH+). HPLC: Rt: 3.62 min.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionThe resulting residue was diluted with 120 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=1:1)

Sources & evidence

ORD record
ord-f47a8738de3d409a86311e2a87d4b253
Source dataset
uspto-grants-2012_05
Patent number
US08168794B2

Reaction notes

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