Trifluoroacetic acid → HCID 18723226, compound

HRID 522858Notes

Reaction equation

HRID 522858 reaction equation
[F:1][C:2]([F:26])([F:25])[O:3][C:4]1[CH:24]=[CH:23][C:7]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:25][C:2]([F:1])([F:26])[O:3][C:4]1[CH:24]=[CH:23][C:7]([CH2:8][O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18723402HCID 18723402, compound

Product 1

HCID 18723226HCID 18723226, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(4-(trifluoromethoxy)benzyloxy)piperidine-1-carboxylate was dissolved in CH2Cl2 (40 mL) and TFA (4 mL) was added. The light yellow solution was stirred at RT for 20 h, after which time complete Boc deprotection was evident by LC-MS. The solution was concentrated under reduced pressure providing product as a TFA salt in 65-95% overall yield. The material was purified to obtain a salt or free based using catch and release with strong cation exchange chromatography (SCX-2) washing first with MeOH, then with 2M NH3 in MeOH.

Workup

  1. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1e3af4f069fd4273b1e7fe41a062ab83
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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