Hydrochloric Acid → HCID 118207436, compound

HRID 1507238Notes

Reaction equation

HRID 1507238 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][C@H:16]2[F:28])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:29]>O1CCOCC1>[ClH:29].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[CH2:20][CH2:19][NH:18][CH2:17][C@H:16]2[F:28])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 118207469HCID 118207469, compound

Product 1

HCID 118207436HCID 118207436, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of (3S,4S)-t-butyl 4-(4-(benzyloxy)phenyl)-3-fluoropiperidine-1-carboxylate (0.12 g, 0.31 mmol, E-1 from step E) in 1,4-dioxane (3 mL) was added a 4 M HCl in dioxane solution (2 mL, 8 mmol) and the reaction mixture was stirred at rt overnight. The mixture was concentrated in vacuo and the solid was triturated with ethyl acetate and dried to afford E-1a (3S,4S)-4-(4-(benzyloxy)phenyl)-3-fluoropiperidine hydrochloride (0.09 g, 88% yield) as an off-white solid. LCMS (method P) RT 0.95 min, m/z 286 (M+H+; 400 MHz, DMSO-d6: δ 1.94-1.96 (m, 2H), 2.97-3.04 (m, 3H), 3.38-3.62 (m, 2H), 4.84-4.95 (m, 1H), 5.10 (s, 2H), 7.00-7.03 (m, 2H), 7.17-7.20 (m, 2H), 7.31-7.46 (m, 5H), 9.30 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe solid was triturated with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-caf56a72f56649d489eecb96b5adfce0
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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