3-(Chloromethyl)-1-methoxynaphthalene → HCID 67220445, compound

HRID 1838712Notes

Reaction equation

HRID 1838712 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([OH:14])[C@@H:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]#[N:33])=[CH:17][CH:16]=2)[C@H:10]([O:34][CH2:35][C@H:36]2[CH2:40][O:39][C:38]([CH3:42])([CH3:41])[O:37]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:44][C:45]1[CH:46]=[C:47]([O:55][CH3:56])[C:48]2[C:53]([CH:54]=1)=[CH:52][CH:51]=[CH:50][CH:49]=2>>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([O:14][CH2:44][C:45]2[CH:46]=[C:47]([O:55][CH3:56])[C:48]3[C:53](=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH:54]=2)[C@@H:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][O:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]#[N:33])=[CH:17][CH:16]=2)[C@H:10]([O:34][CH2:35][C@H:36]2[CH2:40][O:39][C:38]([CH3:42])([CH3:41])[O:37]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 187554433-(Chloromethyl)-1-methoxynaphthaleneHCID 57006381HCID 57006381, compound

Product 1

HCID 67220445HCID 67220445, compound

Procedure

In analogy to the procedure described in example 1) (f) the (3S,4R,5R)-4-[4-[3-(2-cyano-phenoxy)-propoxy]-phenyl]-3-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-5-hydroxy-piperidine-1-carboxylic acid tert-butyl ester was reacted with 3-chloromethyl-1-methoxy-naphthalene [example 1 (α)] to yield the (3S,4R,5R)-4-[4-[3-(2-cyano-phenoxy)-propoxy]-phenyl]-3-[(4S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-5-(4-methoxy-naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid tert-butyl ester as colorless oil; MS: 753 (M+H)+.

Sources & evidence

ORD record
ord-106431be3bd049ee889aa05a156ac1f1
Source dataset
uspto-grants-2004_01
Patent number
US06673931B2

Reaction notes

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