1-(t-Butoxycarbonyl)4-((2-benzyl)tetrazol-5-yl)piperidine → 4-((2-Benzyl)tetrazol-5-yl)piperidine

HRID 278237Notes

Reaction equation

HRID 278237 reaction equation
[C:1]([O:5]C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]=[N:16][N:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH2:26]([Cl:28])[Cl:27].C(O)(C(F)(F)F)=[O:30]>>[CH2:26]([Cl:28])[Cl:27].[CH3:1][OH:5].[NH4+:8].[OH-:30].[CH2:19]([N:17]1[N:16]=[N:15][C:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[N:18]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 181875061-(t-Butoxycarbonyl)4-((2-benzyl)tetrazol-5-yl)piperidineHCID 21863450Trifluoroacetic acid methylene chloride

Product 2

HCID 181874764-((2-Benzyl)tetrazol-5-yl)piperidineYield 94%HCID 21896990Dichloromethane methanol ammonium hydroxide

Procedure

A solution of 85 mg (0.25 mmol) of 1-(t-butoxycarbonyl)-4-((2-benzyl)tetrazol-5-yl)piperidine (from Step C) in 2 mL of 1:1 v/v methylene chloride/TFA was stirred at rt for 2 h. The solution was concentrated. Flash chromatography on silica gel using 19:1:0.1 v/v/v methylene chloride/methanol/NH4OH as the Eluant afforded 57 mg (94%) of the title compound.

Workup

  1. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-f48d7bbaccd24143b898f4ce52a2535b
Source dataset
uspto-grants-2002_03
Patent number
US06358979B1

Reaction notes

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