Water → 1-Amino-3-(tetrahydro-2H-pyran-2-yloxy)octane
Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:9][C:10]#[N:11].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC>[NH2:11][CH2:10][CH2:9][CH:8]([O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]Participants
Conditions
- Temperature
- 25 °C
Procedure
A solution of 3-(tetrahydro-2H-pyran-2-yloxy)-caprylonitrile (4.05 g., 18 millimole) in dry ether (10 ml.) is added dropwise to a stirred suspension of lithium aluminum hydride (0.76 g., 20 millimole) in dry ether (90 ml.) maintained under a nitrogen atmosphere. Upon completion of the addition, the reaction mixture is stirred and heated at reflux for 16 hours. After cooling to 25° C., the reaction mixture is treated successively with water (1 ml.), and 5% aqueous sodium hydroxide (3 ml.) added dropwise with caution, affording a fine suspension which is cooled to and maintained at 0°-5° C. for 30 minutes, and filtered. In vacuo evaporation of the solvent leaves the title compound as a pale yellow oil (3.95 g., 95%), pmr (CDCl3) δ 0.88 (3H, t), 2.79 (2H, m) and 4.68 (H, bs).
Workup
- temperaturemaintained under a nitrogen atmosphere
- additionUpon completion of the addition
- temperatureheated
- temperatureat reflux for 16 hours
- additionadded dropwise with caution
- customaffording a fine suspension which
- temperatureis cooled to and
- temperaturemaintained at 0°-5° C. for 30 minutes
- filtrationfiltered
- customIn vacuo evaporation of the solvent
Sources & evidence
- ORD record
- ord-8cf3051daa8e4102b7e76ff2b0fd592a
- Source dataset
- uspto-grants-1981_04
- Patent number
- US04260771
Reaction notes
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