Trifluoroacetic acid → (3S)-3-(piperidine-1-carbonyl)-1,2,3,4-tetrahydroisoquinoline

HRID 132833Notes

Reaction equation

HRID 132833 reaction equation
CC(OC([N:8]1[C@H:17]([C:18]([OH:20])=O)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)C.[CH:21]1[CH:22]=[CH:23]C2N(O)N=[N:27][C:25]=2[CH:26]=1.C(N(CC)C(C)C)(C)C.N1CCCCC1.FC(F)(F)C(O)=O>C(Cl)CCl>[N:27]1([C:18]([C@@H:17]2[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:9][NH:8]2)=[O:20])[CH2:23][CH2:22][CH2:21][CH2:26][CH2:25]1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 8082PiperidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 664088(3S)-2-((tert-butoxy)carbonyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 10657955(3S)-3-(piperidine-1-carbonyl)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Following a procedure similar to that described for Intermediate 14, treatment of Boc-TIC-OH with EDC, HOBt, N,N-diisopropylethylamine and piperidine, followed by deprotection using trifluoroacetic acid, afforded the title compound as a white foam. LC/MS: 245.2 (M+1).

Sources & evidence

ORD record
ord-e1fd4f18821741ddab6a8ef7d71ad754
Source dataset
uspto-grants-2008_06
Patent number
US07388019B2

Reaction notes

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