Hydrochloric Acid → HCID 22127919, compound

HRID 1858765Notes

Reaction equation

HRID 1858765 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11](C(OCC[Si](C)(C)C)=O)[CH2:10][CH:9]2[O:23][CH2:24][C:25]2[CH:34]=[C:33]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([O:43]COCC[Si](C)(C)C)[CH:38]=3)[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>FC1C=CC(C2CCNCC2OCC2C=C(OCC3C=CC=C(OCOCC[Si](C)(C)C)C=3)C3C(=CC=CC=3)C=2)=CC=1.O1CCCC1.CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH:9]2[O:23][CH2:24][C:25]2[CH:34]=[C:33]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][CH:40]=[C:39]([OH:43])[CH:38]=3)[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 54557925HCID 54557925, compound

Product 1

HCID 22127919HCID 22127919, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 86755338HCID 86755338, compoundSolvent

Procedure

From 2-trimethylsilylethyl (3RS,4RS)-4-(4-fluorophenyl)-3-[4-[3-(2-trimethylsilyl-ethoxymethoxy)-benzyloxy]-naphthalen-2-ylmethoxy]-piperidine-1-carboxylate there was obtained in analogy to the procedure described in Example 1(e) by cleavage of the 2-trimethylsilylethyl carbamate with tetrabutyl-ammonium fluoride in tetrahydrofuran (3RS,4RS)-4-(4-fluorophenyl)-3-[4-[3-(2-trimethylsilyl-ethoxymethoxy)-benzyloxy]-naphthalen-2-ylmethoxy]-piperidine, MS: 588 (M+H)+, as a light yellow oil, from which by cleavage of the SEM group by means of a 2N solution of hydrogen chloride in methanol analogously to the procedure described in Example 5(g) there was obtained (3RS,4RS)-4-(4-fluorophenyl)-3-[4-[3-hydroxy-benzyloxy]-naphthalen-2-ylmethoxy]-piperidine as a colourless solid; MS: 458 (M+H)+.

Sources & evidence

ORD record
ord-05bf93bee46b4c7faf2692111bb6145b
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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