1-[2-[7-[(3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidin-3-yloxymethyl]-naphthalen-2-yloxy]-ethyl]-4-methyl-piperazine → (3R,4R)-4-(4-hydroxy-phenyl)-piperidin-3-ol hydrochloride

HRID 650720Notes

Reaction equation

HRID 650720 reaction equation
[ClH:1].C([O:9][C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[CH2:21][CH2:20][N:19]([C@@H](C3C=CC=CC=3)C)[CH2:18][C@@H:17]2[OH:30])=[CH:12][CH:11]=1)C1C=CC=CC=1.COC1C=CC=CC=1COCCCOC1C=CC([C@H]2CCNC[C@@H]2OCC2C=C3C(C=CC(OCCN4CCN(C)CC4)=C3)=CC=2)=CC=1.[H][H]>>[ClH:1].[OH:9][C:10]1[CH:15]=[CH:14][C:13]([C@H:16]2[CH2:21][CH2:20][NH:19][CH2:18][C@@H:17]2[OH:30])=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 98525821-[2-[7-[(3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidin-3-yloxymethyl]-naphthalen-2-yloxy]-ethyl]-4-methyl-piperazineHCID 69110291(3R,4R)-1-[(1R)-1-Phenylethyl]-4-[4-(phenylmethoxy)phenyl]-3-piperidinol hydrochloride2×HCID 178418361HCID 178418361, compound

Product 1

HCID 20677893(3R,4R)-4-(4-hydroxy-phenyl)-piperidin-3-ol hydrochloride

Procedure

Another preferred aspect of the present invention is the transformation of (3R,4R)-4-(4-benzyloxy-phenyl)-1-((R)-1-phenyl-ethyl)-piperidin-3-ol hydrochloride to 1-[2-[7-[(3R,4R)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidin-3-yloxymethyl]-naphthalen-2-yloxy]-ethyl]-4-methyl-piperazine by the following procedure: a) reacting (3R,4R)-4-(4-benzyloxy-phenyl)-1-((R)-1-phenyl-ethyl)-piperidin-3-ol hydrochloride with hydrogen to yield (3R,4R)-4-(4-hydroxy-phenyl)-piperidin-3-ol hydrochloride;

Sources & evidence

ORD record
ord-8187165658cb4c29b93b5ffa61c23d69
Source dataset
uspto-grants-2001_08
Patent number
US06274735B1

Reaction notes

Loading…