1,4-Dioxane hydrochloride → (1S)-1-(Oxan-4-yl)ethan-1-amine

HRID 2206638Notes

Reaction equation

HRID 2206638 reaction equation
CC([S@]([NH:7][CH:8]([CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)[CH3:9])=O)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[O:13]1[CH2:14][CH2:15][CH:10]([C@@H:8]([NH2:7])[CH3:9])[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 89739114HCID 89739114, compound

Product 1

HCID 67033300(1S)-1-(Oxan-4-yl)ethan-1-amineYield 150.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-methyl-N-(1-(tetrahydro-2H-pyran-4-yl)ethyl)Propane-2-sulfinamide (1.2 g) in CH2Cl2 (4 mL) was added HCl-dioxane (4 mL) at 25° C. The reaction was stirred for 2 hrs. Then the mixture was concentrated in vacuo, diluted with water and washed with ethyl acetate to give crude (S)-1-(tetrahydro-2H-pyran-4-yl)ethanamine (1.0 g) as a yellow oil.

Workup

  1. concentrationThen the mixture was concentrated in vacuo
  2. additiondiluted with water
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-673f8ea57a9545458ab02013c64bcabb
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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