1,4-Dioxane → HCID 68478946, compound

HRID 238346Notes

Reaction equation

HRID 238346 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:23])[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][C@@:9]2([OH:22])[CH3:21])=[CH:4][CH:3]=1.O1CCOCC1>Cl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:23])[CH2:13][CH2:12][NH:11][CH2:10][C@:9]2([CH3:21])[OH:22])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 59444290HCID 59444290, compound

Product 1

HCID 68478946HCID 68478946, compoundYield 201%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (3S,4S)-tert-butyl 4-(4-chlorophenyl)-3,4-dihydroxy-3-methylpiperidine-1-carboxylate (2.08 g, 6.08 mmol) in 4 M HCl in dioxane (30.4 mL, 122 mmol) was stirred at room temperature for 45 minutes. The mixture was concentrated in vacuo, then concentrated from methylene chloride (3×) to remove residual HCl, to yield (3S,4S)-4-(4-chlorophenyl)-3-methylpiperidine-3,4-diol hydrochloride (1.7 g, 6.11 mmol, 100% yield) as a powder. 1H NMR (400 MHz, MeOD4) δ 7.55 (d, J=8.8 Hz, 2H), 7.36 (d, J=8.8 Hz, 2H), 3.42 (m, 1H), 3.29 (m, 1H), 3.05 (d, J=13.2 Hz, 1H), 2.71 (ddd, J=13.2, 4.8 Hz, 1H), 1.97 (dt, J=14.5, 3.1 Hz, 1H), 1.08 (s, 3H); m/z (ES+)=242.1 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. concentrationconcentrated from methylene chloride (3×)
  3. customto remove residual HCl

Sources & evidence

ORD record
ord-9fa2281be34841b097c865df693b9b4c
Source dataset
uspto-grants-2014_02
Patent number
US08642622B2

Reaction notes

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