Hydrochloric Acid → HCID 59455657, compound

HRID 69981Notes

Reaction equation

HRID 69981 reaction equation
[Si]([O:8][C@@H:9]1[CH2:14][C@@H:13]([F:15])[CH2:12][NH:11][CH2:10]1)(C(C)(C)C)(C)C.Cl.[CH:17]([OH:20])([CH3:19])C.[CH3:21][OH:22]>>[F:15][C@@H:13]1[CH2:14][C@@H:9]([OH:8])[CH2:10][N:11]([C:21]([O:20][CH2:17][C:19]2[CH:10]=[CH:9][CH:14]=[CH:13][CH:12]=2)=[O:22])[CH2:12]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3776IsopropanolHCID 59455637(3R,5R)-3-(tert-butyldimethylsilyloxy)-5-fluoropiperidine

Product 1

HCID 59455657HCID 59455657, compoundYield 94%

Procedure

To a solution of (3R,5R)-3-(tert-butyldimethylsilyloxy)-5-fluoropiperidine (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=2:1) to give (3R,5R)-benzyl 3-fluoro-5-hydroxypiperidine-1-carboxylate, (94%). LC/MS (m/z): 254.2 (MH+).

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=2:1)

Sources & evidence

ORD record
ord-46fa03659f6446bc980bca26afd9ea51
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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