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

HRID 272899Notes

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

Participants

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

temperatureThe reaction mixture was heated
temperatureto reflux for 2 h
filtrationthe mixture was filtered over diatomaceous earth
concentrationconcentrated
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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