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

HRID 1858752Notes

Reaction equation

HRID 1858752 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(OC(N1CCC(C2C=CC=CC=2OCCCOCC2C=CC=CC=2OC)C(OCC2C=CC3C(=CC(OCOCC[Si](C)(C)C)=CC=3)C=2)C1)=O)(C)(C)C.[C:110]([O:114][C:115]([N:117]1[CH2:122][CH2:121][CH:120]([C:123]2[CH:128]=[CH:127][C:126]([O:129][CH2:130][CH2:131][CH2:132][O:133][CH2:134][C:135]3[CH:140]=[CH:139][CH:138]=[CH:137][C:136]=3[O:141][CH3:142])=[CH:125][CH:124]=2)[CH:119]([O:143][CH2:144][C:145]2[CH:154]=[CH:153][C:152]3[C:147](=[CH:148][C:149]([O:155]COCC[Si](C)(C)C)=[CH:150][CH:151]=3)[CH:146]=2)[CH2:118]1)=[O:116])([CH3:113])([CH3:112])[CH3:111]>>[C:110]([O:114][C:115]([N:117]1[CH2:122][CH2:121][CH:120]([C:123]2[CH:128]=[CH:127][C:126]([O:129][CH2:130][CH2:131][CH2:132][O:133][CH2:134][C:135]3[CH:140]=[CH:139][CH:138]=[CH:137][C:136]=3[O:141][CH3:142])=[CH:125][CH:124]=2)[CH:119]([O:143][CH2:144][C:145]2[CH:154]=[CH:153][C:152]3[C:147](=[CH:148][C:149]([OH:155])=[CH:150][CH:151]=3)[CH:146]=2)[CH2:118]1)=[O:116])([CH3:113])([CH3:111])[CH3:112]

Participants

5

Reactant 4

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-butylesterHCID 86756064HCID 86756064, compound

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) (α)] 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-67794aaacc5047f2bb13ccc5cb8193f0
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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