Hydrochloric Acid → (1R,3S)-3-[(benzyloxy)methyl]cyclopentanamine hydrochloride

HRID 45256Notes

Reaction equation

HRID 45256 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[CH2:14][CH2:13][C@@H:12]([NH:15]C(=O)OC(C)(C)C)[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:23]>C(Cl)Cl.O1CCOCC1.CCOCC>[ClH:23].[CH2:1]([O:8][CH2:9][C@H:10]1[CH2:14][CH2:13][C@@H:12]([NH2:15])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 86659749tert-butyl {(1R,3S)-3-[(benzyloxy)methyl]cyclopentyl}carbamate

Product 1

HCID 86659750(1R,3S)-3-[(benzyloxy)methyl]cyclopentanamine hydrochlorideYield 83%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1.52 g (5 mmol) of tert-butyl {(1R,3S)-3-[(benzyloxy)methyl]-cyclopentyl}carbamate in 20 mL of DCM are added, at 0° C., 5 mL (20 mmol) of a 4N solution of HCl in dioxane. The medium is then stirred for 12 hours at room temperature, and then concentrated under reduced pressure. The residue obtained is solidified in 20 mL of Et2O, filtered and dried under vacuum. 1 g of (1R,3S)-3-[(benzyloxy)methyl]cyclopentanamine hydrochloride is obtained in the form of a powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue obtained
  3. filtrationfiltered
  4. customdried under vacuum

Sources & evidence

ORD record
ord-5745c52988ee49dd96e9759d61f7dddb
Source dataset
uspto-grants-2013_09
Patent number
US08541455B2

Reaction notes

Loading…