Hydrochloric Acid → HCID 69314333, compound

HRID 2214313Notes

Reaction equation

HRID 2214313 reaction equation
[C:1]([Si:5]([CH3:43])([CH3:42])[O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:16]([CH:17]([OH:33])[C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:20][CH:19]=3)=[C:15]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3O)[CH2:14][CH2:13][O:12][C:11]=2[CH:41]=1)([CH3:4])([CH3:3])[CH3:2].Cl>C1(C)C=CC=CC=1>[C:1]([Si:5]([CH3:43])([CH3:42])[O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:16]3[CH:17]([C:18]4[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][N:27]5[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]5)=[CH:22][CH:23]=4)[O:33][C:35]4[C:34](=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:15]=3[CH2:14][CH2:13][O:12][C:11]=2[CH:41]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21959160HCID 21959160, compound

Product 1

HCID 69314333HCID 69314333, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Following the procedure described in Examples 76, 2-(tert-Butyl-dimethyl-silyloxy)-11,12-dihydro-5H-6,13-dioxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-5-ol, the compound prepared as in Example 105 above, was reacted with 1-[2-(4-Iodo-phenoxy)-ethyl]-piperidine to yield 2-(8-(tert-Butyl-dimethyl-silyloxy)-5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-2,3-dihydro-benzo[b]oxepin-4-yl)-phenol as a crude oil. The crude 2-(8-(tert-Butyl-dimethyl-silyloxy)-5-{hydroxy-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methyl}-2,3-dihydro-benzo[b]oxepin-4-yl)-phenol was then further treated with HCl (12N, 4 eq., 0.67 mL) in toluene (100 mL) to generate yield 1-(2-{4-[2-(tert-Butyl-dimethyl-silyloxy)-11,12-dihydro-5H-6,13-dioxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-5-yl]-phenoxy}-ethyl)-piperidine as a crude oil. The crude 1-(2-{4-[2-(tert-Butyl-dimethyl-silyloxy)-11,12-dihydro-5H-6,13-dioxa-benzo[3,4]cyclohepta[1,2-a]naphthalen-5-yl]-phenoxy}-ethyl)-piperidine was then further treated with HF•Pyridine (70% HF, 30% Pyridine, 0.5 mL) in CH3CN (20 mL) at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate:THF (1:1) and then washed with 5% NaHCO3 and brine. The reaction mixture was dried, concentrated and purified by flash chromatograph eluted with 5% MeOH in DCM to yield the title compound as a slightly yellow solid.

Sources & evidence

ORD record
ord-d0100713045e48769abaf8a2924363ca
Source dataset
uspto-grants-2006_09
Patent number
US07105679B2

Reaction notes

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