Hydrochloric Acid → (R)-1-[(3S,4R,5R)-4-[4-[3-(5-fluoro-2-methoxy-benzyloxy)-propoxy]-phenyl]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidin-3-yloxy]-3-methoxy-propan-2-ol

HRID 843447Notes

Reaction equation

HRID 843447 reaction equation
C(OC([N:8]1[CH2:13][C@H:12]([O:14][CH2:15][C:16]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)[C@@H:11]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][CH2:37][O:38][CH2:39][C:40]3[CH:45]=[C:44]([F:46])[CH:43]=[CH:42][C:41]=3[O:47][CH3:48])=[CH:30][CH:29]=2)[C@H:10]([O:49][CH2:50][C@H:51]([OH:55])[CH2:52][O:53][CH3:54])[CH2:9]1)=O)(C)(C)C.Cl>CO>[F:46][C:44]1[CH:43]=[CH:42][C:41]([O:47][CH3:48])=[C:40]([CH:45]=1)[CH2:39][O:38][CH2:37][CH2:36][CH2:35][O:34][C:31]1[CH:32]=[CH:33][C:28]([C@@H:11]2[C@@H:12]([O:14][CH2:15][C:16]3[CH:25]=[C:24]([O:26][CH3:27])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)[CH2:13][NH:8][CH2:9][C@H:10]2[O:49][CH2:50][C@H:51]([OH:55])[CH2:52][O:53][CH3:54])=[CH:29][CH:30]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57004131HCID 57004131, compound

Product 1

HCID 57198364(R)-1-[(3S,4R,5R)-4-[4-[3-(5-fluoro-2-methoxy-benzyloxy)-propoxy]-phenyl]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidin-3-yloxy]-3-methoxy-propan-2-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In analogy to the procedure described in example 1(l) the (3S,4R,5R)-4-{4-[3-(5-fluoro-2-methoxy-benzyloxy)-propoxy]-phenyl}-3-[(2R)-2-hydroxy-3-methoxy-propoxy]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester was deprotected with hydrochloric acid in methanol to yield the (R)-1-[(3S,4R,5R)-4-[4-[3-(5-fluoro-2-methoxy-benzyloxy)-propoxy]-phenyl]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidin-3-yloxy]-3-methoxy-propan-2-ol as colorless oil; MS: 664 (M+H)+.

Sources & evidence

ORD record
ord-ee919f03f1c6496485f6ab7dfb390541
Source dataset
uspto-grants-2002_04
Patent number
US06376672B1

Reaction notes

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