Trifluoroacetic acid → HCID 15546932, compound

HRID 1005230Notes

Reaction equation

HRID 1005230 reaction equation
BrCC1C=CC2C(=CC=CC=2)C=1.[CH2:13]([O:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]2[CH:36]([CH2:37][O:38]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:35][N:34]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[CH2:33][CH:32]2[O:65][CH2:66][C:67]2[CH:76]=[CH:75][C:74]3[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=3)[CH:68]=2)=[CH:27][CH:26]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.FC(F)(F)C(O)=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[CH2:13]([O:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([CH:31]2[CH:32]([O:65][CH2:66][C:67]3[CH:76]=[CH:75][C:74]4[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=4)[CH:68]=3)[CH2:33][N:34]([C:58]([O:60][C:61]([CH3:62])([CH3:64])[CH3:63])=[O:59])[CH2:35][CH:36]2[CH2:37][OH:38])=[CH:29][CH:30]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 9845Trifluoroacetic anhydrideHCID 703202-BromomethylnaphthaleneHCID 86604524HCID 86604524, compound

Product 1

HCID 15546932HCID 15546932, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an analogous manner to that described in Example 22 (h), by reacting tert-butyl (3RS,4RS,5SR)-4-[4-(3-benzyloxy-propoxy)-phenyl]-3-hydroxy-5-hydroxymethyl-piperidine-1-carboxylate with triphenylchloromethane in pyridine there was obtained tert-butyl (3RS,4RS,5SR)-4-[4-(3-benzyloxy-propoxy)-phenyl]-3-hydroxy-5-trityloxymethyl-piperidine-1-carboxylate, [MS: 731 (M+NH4)+ ], as a colourless foam, alkylation of which with 2-bromomethyl-naphthalene analogously to Example 62 (h) gave tert-butyl (3RS,4RS,5SR)-4-[4-(3-benzyloxy-propoxy)-phenyl]-3-(naphthalen-2-ylmethoxy)-5-trityloxymethyl-piperidine-1-carboxylate, [MS: 871 (M+NH4)+ ], as a colourless foam. Subsequent selective cleavage of the trityl group by means of a mixture of trifluoroacetic acid and trifluoroacetic anhydride in methylene chloride analogously to Example 86 (u) yielded tert-butyl (3SR,4RS,5RS)-4-[4-(3-benzyloxy-propoxy)-phenyl]-3-hydroxymethyl-5-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate as a colourless solid; MS: 612 (M+H)+. Subsequent alkylation with methyl iodide analogously to Example 62 (h) gave tert-butyl (3SR,4RS,5RS)-4-[4-(3-benzyloxy-propoxy)-phenyl]-3-methoxymethyl-5-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylate as a colourless solid; MS: 626 (M+H)+.

Sources & evidence

ORD record
ord-ee7c511639f34e3d9c9366227804a037
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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