Hydrochloric Acid → 5-Aminocyclooctan-1-ol

HRID 402545Notes

Reaction equation

HRID 402545 reaction equation
Cl.C([Si](C)(C)[O:7][CH:8]1[CH2:15][CH2:14][CH2:13][CH:12]([NH2:16])[CH2:11][CH2:10][CH2:9]1)(C)(C)C>CC(O)C>[NH2:16][CH:12]1[CH2:13][CH2:14][CH2:15][CH:8]([OH:7])[CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 592248345-(tert-Butyl-dimethyl-silanyloxy)-cyclooctylamine

Product 1

HCID 214902395-Aminocyclooctan-1-olYield 138.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

35 mL of 2N aqueous hydrochloric acid were added to a solution of 3.5 g (13.6 mmol) of 5-(tert-butyl-dimethyl-silanyloxy)-cyclooctylamine (59) in 35 mL 2-propanol and the resulting solution was stirred at room temperature overnight. The isopropanol was removed under reduced pressure and the resulting aqueous solution washed with t-butylmethylether. 2.7 g of crude 5-amino-cyclooctanol (60) was obtained by freeze-drying the aqueous layer as a diastereomeric mixture as hydrochloride which was used without further purification. Rt=0.18 min (Method C). Detected mass: 144.2 (M+H+).

Workup

  1. customThe isopropanol was removed under reduced pressure
  2. washthe resulting aqueous solution washed with t-butylmethylether

Sources & evidence

ORD record
ord-154e3a4420184878b1f60e8dace4cd99
Source dataset
uspto-grants-2014_06
Patent number
US08742116B2

Reaction notes

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