Tert-butyl 4-(2-pyrrolidin-1-ylethoxymethyl)piperidine-1-carboxylate → 4-(2-Pyrrolidin-1-ylethoxymethyl)piperidine

HRID 928574Notes

Reaction equation

HRID 928574 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N:1]1([CH2:6][CH2:7][O:8][CH2:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 89579709Tert-butyl 4-(2-pyrrolidin-1-ylethoxymethyl)piperidine-1-carboxylate

Product 1

HCID 623388724-(2-Pyrrolidin-1-ylethoxymethyl)piperidineYield 72.9%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

Tert-butyl 4-(2-pyrrolidin-1-ylethoxymethyl)piperidine-1-carboxylate (5.28 g, 0.017 moles) was stirred at room temperature in TFA/DCM (1:1, 40 mL) for 1 hour. The solvent was removed at reduced pressure. The resulting residue was purified using an SCX column to afford 4-(2-pyrrolidin-1-ylethoxymethyl)piperidine (2.63 g). LCMS [M+H]+=213.2

Workup

  1. customThe solvent was removed at reduced pressure
  2. customThe resulting residue was purified

Sources & evidence

ORD record
ord-fc52f5d4c4c6400fac31c082aa57f79b
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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