Hydrochloric Acid → 4-((1R,2R)-2-((3-fluoro-4-(1H-tetrazol-1-yl)benzyloxy)methyl)cyclopropyl)piperidinium chloride

HRID 1468870Notes

Reaction equation

HRID 1468870 reaction equation
[ClH:1].O1CCOCC1.[F:8][C:9]1[CH:10]=[C:11]([CH:31]=[CH:32][C:33]=1[N:34]1[CH:38]=[N:37][N:36]=[N:35]1)[CH2:12][O:13][CH2:14][C@@H:15]1[CH2:17][C@@H:16]1[CH:18]1[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]1>C(Cl)Cl>[Cl-:1].[F:8][C:9]1[CH:10]=[C:11]([CH:31]=[CH:32][C:33]=1[N:34]1[CH:38]=[N:37][N:36]=[N:35]1)[CH2:12][O:13][CH2:14][C@@H:15]1[CH2:17][C@@H:16]1[CH:18]1[CH2:23][CH2:22][NH2+:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 71140737tert-butyl 4-((1R,2R)-2-((3-fluoro-4-(1H-tetrazol-1-yl)benzyloxy)methyl)cyclopropyl)piperidine-1-carboxylate

Product 1

HCID 711160804-((1R,2R)-2-((3-fluoro-4-(1H-tetrazol-1-yl)benzyloxy)methyl)cyclopropyl)piperidinium chlorideYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4 M HCl in dioxane (2.4 mL, 9.62 mmol) was added to a solution of tert-butyl 4-((1R,2R)-2-((3-fluoro-4-(1H-tetrazol-1-yl)benzyloxy)methyl)cyclopropyl)piperidine-1-carboxylate (Step C product, 415 mg, 0.962 mmol) in DCM (3 mL). This mixture was stirred at rt for 1 hr. The reaction mixture was subsequently concentrated under reduced pressure to afford the title compound (351 mg, 99%) as a crude product to be used for the next step. LC/MS (m/z): 332 (M+H)+.

Workup

  1. concentrationThe reaction mixture was subsequently concentrated under reduced pressure

Sources & evidence

ORD record
ord-3c1a9ab6816d46c598f321a64c7992e6
Source dataset
uspto-grants-2015_04
Patent number
US09006228B2

Reaction notes

Loading…