Water → 1-Amino-3-(tetrahydro-2H-pyran-2-yloxy)octane

HRID 2397611Notes

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].[Li].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 aluminumhydride (0.76 g., 20 millimole) in dry ether (90 ml.) maintained under a nitrogen atmosphere. Upon completing 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 (CDCl 3) δ 0.88 (3H, t), 2.79 (2H, m) and 4.68 (H, bs).

Workup

temperaturemaintained under a nitrogen atmosphere
additionthe 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-e9a9b92512bf4e15962131d1c4784c1e
Source dataset: uspto-grants-1977_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04022794

Reaction notes

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