2-Chloromethyl-7-(2-trimethylsilanyl-ethoxymethoxy)-naphthalene → HCID 57161469, compound

HRID 1005133Notes

Reaction equation

HRID 1005133 reaction equation
C(OC(N1CCC(C2C=CC(OCCCOCC3C=CC=CC=3OC)=CC=2)C(O)C1)=O)(C)(C)C.ClCC1C=CC2C(=CC(OCOCC[Si](C)(C)C)=CC=2)C=1.[C:56]([O:60][C:61]([N:63]1[CH2:68][CH2:67][CH:66]([C:69]2[CH:74]=[CH:73][C:72]([O:75][CH2:76][CH2:77][CH2:78][O:79][CH2:80][C:81]3[CH:86]=[CH:85][CH:84]=[CH:83][C:82]=3[O:87][CH3:88])=[CH:71][CH:70]=2)[CH:65]([O:89][CH2:90][C:91]2[CH:100]=[CH:99][C:98]3[C:93](=[CH:94][C:95]([O:101]COCC[Si](C)(C)C)=[CH:96][CH:97]=3)[CH:92]=2)[CH2:64]1)=[O:62])([CH3:59])([CH3:58])[CH3:57]>>[C:56]([O:60][C:61]([N:63]1[CH2:68][CH2:67][CH:66]([C:69]2[CH:74]=[CH:73][C:72]([O:75][CH2:76][CH2:77][CH2:78][O:79][CH2:80][C:81]3[CH:86]=[CH:85][CH:84]=[CH:83][C:82]=3[O:87][CH3:88])=[CH:71][CH:70]=2)[CH:65]([O:89][CH2:90][C:91]2[CH:100]=[CH:99][C:98]3[C:93](=[CH:94][C:95]([OH:101])=[CH:96][CH:97]=3)[CH:92]=2)[CH2:64]1)=[O:62])([CH3:59])([CH3:57])[CH3:58]

Participants

4

Reactant 3

HCID 111630832-Chloromethyl-7-(2-trimethylsilanyl-ethoxymethoxy)-naphthaleneHCID 15546933Tert-butyl 3-hydroxy-4-{4-[3-(2-methoxybenzyloxy) propoxy]phenyl}piperidine-1-carboxylateHCID 54011448(3RS,4RS)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-[7-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-ylmethoxy]-piperidin-1-carboxylic acid tert-butylester2×

Product 1

HCID 57161469HCID 57161469, compound

Procedure

in an analogeous manner as described in Example 95 (a) there was obtained from (3RS,4RS)-3-hydroxy-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-piperidin-1-carboxylic acid tert-butylester [Example 120 (g) (a)] and 2-chloromethyl-7-(2-trimethylsilanyl-ethoxymethoxy)-naphthalene [Example 6 (u)] (3RS,4RS)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-[7-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-ylmethoxy]-piperidin-1-carboxylic acid tert-butylester as a pale yellow oil; MS: 758 (M+H)+. Then, (3RS,4RS)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-[7-(2-trimethylsilanyl-ethoxymethoxy)-naphthalen-2-ylmethoxy]-piperidin-1-carboxylic acid tert-butylester was reacted in analogy to Example 95 (b) by cleaving of the SEM protecting group to afford (3RS,4RS)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-(7-hydroxy-naphthalen-2-ylmethoxy)-piperidin-1-carboxylic acid tert-butylester [yellow oil; MS: 628 (M+H)+] which, on alkylation with 1-(2-chloro-ethyl)-4-methyl-piperazine hydrochloride (1:2) [Chim. Ther. 4, 283 (1969)] in analogy to Example 90 (n) gave (3RS,4RS)-4-[4-[3-(2-methoxy-benzyloxy)-propoxy]-phenyl]-3-[7-[2-(4-methyl-piperazin-1-yl)-ethoxy]-naphthalen-2-ylmethoxy]-piperidin-1-carboxylic acid tert-butylester as a light brown oil; MS: 754 (M+H)+.

Sources & evidence

ORD record
ord-b66da93711664c25948cc80c2b424462
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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