Water → 1-(4-(Aminomethyl)phenyl)cyclohexanol

HRID 1961441Notes

Reaction equation

HRID 1961441 reaction equation
CC([O-])(C)C.[K+].O.[OH:8][C:9]1([C:15]2[CH:29]=[CH:28][C:18]([CH2:19][NH:20]C(=O)OC(C)(C)C)=[CH:17][CH:16]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>C1COCC1>[NH2:20][CH2:19][C:18]1[CH:17]=[CH:16][C:15]([C:9]2([OH:8])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 66633156Tert-butyl 4-(1-hydroxycyclohexyl)benzylcarbamate

Product 1

HCID 666332311-(4-(Aminomethyl)phenyl)cyclohexanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

355 mg (3.16 mmol) KOtBu and 14 μl (0.79 mmol) H2O were added to a solution of 386 mg (0.79 mmol) tert-butyl 4-(1-hydroxycyclohexyl)benzylcarbamate in 3.9 ml THF. Refluxed for 2 h. Cooled to r.t. The reaction was quenched with NH4Cl (sat.) and the pH was adjusted to 10-11 with 2 M NaOH. The mixture was extracted 3 times with EtOAc. The organic phase was dried (MgSO4) and concentrated. Gave 164 mg (quant. yield). Used directly in the next step.

Workup

  1. temperatureRefluxed for 2 h
  2. customThe reaction was quenched with NH4Cl (sat.)
  3. extractionThe mixture was extracted 3 times with EtOAc
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated
  6. customGave 164 mg (quant. yield)

Sources & evidence

ORD record
ord-a1ac5d0738f64a26b390698d402fcd58
Source dataset
uspto-grants-2013_04
Patent number
US08415333B2

Reaction notes

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