Hydrochloric Acid → HCID 178511253, compound

HRID 271364Notes

Reaction equation

HRID 271364 reaction equation
[OH:1][CH:2]([C@@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][NH:18]C(=O)OC(C)(C)C)[CH2:13][CH2:12]1)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.[OH-].[Na+]>O1CCOCC1>[NH2:18][CH2:17][C@@H:14]1[CH2:13][CH2:12][C@H:11]([CH:2]([OH:1])[CH2:3][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178453609HCID 178453609, compound

Product 1

HCID 178511253HCID 178511253, compoundYield 109.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of (±)-tert-butyl {[cis-4-(1-hydroxy-3-phenylpropyl)cyclohexyl]methyl}carbamate (3.63 g, approximately 10 mmol) in dioxane (20 ml) cooled in an ice-bath was added dropwise 4M hydrogen choride in dioxane (20 ml, 80 mmol). The solution was stirred 2 hours at ice-bath temperature, one hour at ambient temperature, then concentrated at reduced pressure. The solid residue was taken up in methylene chloride (200 ml) and 10N sodium hydroxide (1.0 ml, 10 mmol) was added. The mixture was stirred 20 minutes at ambient temperature, dried (sodium carbonate and sodium sulfate), filtered, and the solvent evaporated under reduced pressure to give crude (+−)-1-[cis-4-(aminomethyl)cyclohexyl]-3-phenylpropan-1-ol (2.71 g, theoretical yield 2.47 g) as a yellow gum: 1H NMR (CDCl3) 7.28 (2H, m), 7.18 (3H, m), 3.51 (1H, m), 2.85 (1H, m), 2.64 (3H, m), 1.88 (1H, m), 1.69 (1H, m), 1.54-1.33 (3H, m). MS: 248.3 (M+1).

Workup

  1. concentrationconcentrated at reduced pressure
  2. stirringThe mixture was stirred 20 minutes at ambient temperature
  3. dry with materialdried (sodium carbonate and sodium sulfate)
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-1d4add309444492195247183a714cbbe
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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