p-Toluenesulfonic acid → 1-Amino-3-(tetrahydro-2H-pyran-2-yloxy)octane

HRID 28202Notes

Reaction equation

HRID 28202 reaction equation
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:3][C:4]#[N:5].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[NH2:5][CH2:4][CH2:3][CH:2]([O:1][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:11]1)[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 134138033-Hydroxycaprylonitrile

Product 1

HCID 234681061-Amino-3-(tetrahydro-2H-pyran-2-yloxy)octaneYield 95%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3-hydroxycaprylonitrile (5.2 g., 36.8 millimole), dihydropyran (3.8 g., 45 millimole), and p-toluenesulfonic acid.hydrate (catalytic amount) is stirred at 25° C. for 16 hours, then diluted with ether (100 ml.). The resulting solution is washed with 5% aqueous sodium hydroxide (25 ml.) and water (2×25 ml.), dried over magnesium sulfate, and filtered. Evaporation of the filtrate in vacuo affords the title compound as a pale yellow oil (7.9 g., 95%), pmr (CDCl3) δ0.93 (3H, t), 2.54 (2H, q) and 4.68 (H, m).

Workup

  1. washThe resulting solution is washed with 5% aqueous sodium hydroxide (25 ml.) and water (2×25 ml.)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customEvaporation of the filtrate in vacuo

Sources & evidence

ORD record
ord-28614fea5c0f4960b1c76381b08f7f93
Source dataset
uspto-grants-1980_09
Patent number
US04225609

Reaction notes

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