1,4-Dioxane → HCID 68478946, compound

HRID 1888129Notes

Reaction equation

HRID 1888129 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, compound

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 (388 mg, 1.135 mmol) in 4 M HCl in dioxane (10 mL, 40.0 mmol) was stirred at room temperature for 2 hours. The mixture was concentrated in-vacuo, then concentrated 3× from methylene chloride to remove residual HCl and dioxane, to yield the title compound. MS (ESI+)=242.2 (M+H)+, 224.2 (M+H−H2O)+.

Workup

  1. concentrationThe mixture was concentrated in-vacuo
  2. concentrationconcentrated 3× from methylene chloride
  3. customto remove residual HCl and dioxane

Sources & evidence

ORD record
ord-8519f721f6ed41269181e4f058a430d8
Source dataset
uspto-grants-2013_08
Patent number
US08501782B2

Reaction notes

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