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Water → 4-Aminomethyl-4-[4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-cyclohexanol

HRID 272899
Notes
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Reaction equation

HRID 272899 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]=[C:8]1[CH2:13][CH2:12][C:11]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:18][CH:17]=2)([C:14]#[N:15])[CH2:10][CH2:9]1.O.[OH-].[Na+]>C(OCC)C>[NH2:15][CH2:14][C:11]1([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][CH2:25][N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[CH:20][CH:21]=2)[CH2:10][CH2:9][CH:8]([OH:7])[CH2:13][CH2:12]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 230916474-Oxo-1-[4-(3-pyrrolidin-1-ylpropoxy)-phenyl]-cyclohexanecarbonitrile

Product 1

HCID 230916184-Aminomethyl-4-[4-(3-pyrrolidin-1-yl-propoxy)-phenyl]-cyclohexanolYield 54.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of LiAlH4 (0.59 g, 15 mmol, 10 eq) in diethyl ether (8 mL) was added dropwise at ambient temperature a solution of 4-oxo-1-[4-(3-pyrrolidin-1-ylpropoxy)-phenyl]-cyclohexanecarbonitrile (0.5 g, 1.5 mmol) in diethyl ether (25 mL). The reaction mixture was heated to reflux for 2 h. The reaction mixture was cooled to 0° C. and, successively, a solution of water, sodium hydroxide (15% w/v, 0.68 mL) and water again were carefully added dropwise. After being stirred for 15 min at room temperature, the mixture was filtered over diatomaceous earth and concentrated. The residue was purified by flash chromatography (10 g silica gel, DCM/MeOH (10% NH3) to provide the title compound (0.27 g, 54%) as an oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 h
  3. filtrationthe mixture was filtered over diatomaceous earth
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (10 g silica gel, DCM/MeOH (10% NH3)

Sources & evidence

ORD record
ord-e69638cf4b454ec9a1ba8017fb5381dc
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07456164B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes