Trifluoroacetic acid → (R)-1-(piperidin-3-ylmethyl)piperidine

HRID 1643298Notes

Reaction equation

HRID 1643298 reaction equation
[N:1]1([CH2:7][C@@H:8]2[CH2:13][CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:10]1[CH2:11][CH2:12][CH2:13][C@@H:8]([CH2:7][N:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59568770(S)-tert-butyl 3-(piperidin-1-ylmethyl)piperidine-1-carboxylate

Product 1

HCID 26966932(R)-1-(piperidin-3-ylmethyl)piperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of the (S)-tert-butyl 3-(piperidin-1-ylmethyl)piperidine-1-carboxylate isolated above in 200 μL DCM was slowly added 2 mL TFA and the resulting solution stirred for 30 min at 25° C. The solvent was evaporated and the crude product was used directly in the next reaction without further purification. (For example, reaction with Intermediate A5 in Specific Scheme 5)

Workup

  1. customThe solvent was evaporated
  2. customthe crude product was used directly in the next reaction without further purification

Sources & evidence

ORD record
ord-7832b4a468f74217a2b0f49447677f8b
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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