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Water → tert-Butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-9-ylmethoxy)piperidine-1-carboxylate

HRID 1176594
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Reaktionsgleichung

Reaktionsgleichung von HRID 1176594
[CH3:1][O:2][C:3]1[CH:55]=[CH:54][CH:53]=[CH:52][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]2[O:30][CH2:31][C:32]2[C:37]3[N:38](COCC[Si](C)(C)C)[C:39](=[O:43])[CH2:40][CH2:41][CH2:42][C:36]=3[CH:35]=[CH:34][CH:33]=2)=[CH:13][CH:12]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.COC(C)(C)C>O1CCCC1>[CH3:1][O:2][C:3]1[CH:55]=[CH:54][CH:53]=[CH:52][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH:18]2[O:30][CH2:31][C:32]2[C:37]3[NH:38][C:39](=[O:43])[CH2:40][CH2:41][CH2:42][C:36]=3[CH:35]=[CH:34][CH:33]=2)=[CH:15][CH:16]=1
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Komponenten

6

Edukt 4

HCID 962WaterHCID 15413tert-Butyl methyl etherHCID 2724141Tetrabutylammonium Fluoride2×HCID 68503548tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-(2-oxo-1-(2-trimethylsilanylethoxymethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-9-ylmethoxy)piperidine-1-carboxylate

Produkt 1

HCID 68635087
tert-Butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-(2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-9-ylmethoxy)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 0.345 g of tert-butyl 4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}-3-(2-oxo-1-(2-trimethylsilanylethoxymethyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-9-ylmethoxy)piperidine-1-carboxylate in 4 ml of tetrahydrofuran is admixed with 0.85 ml of a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran. The reaction solution is heated to reflux over 4 hours. A further 0.85 ml of tetrabutylammonium fluoride solution is added and the reaction solution is subsequently heated to reflux over a further 20 hours. The reaction solution is cooled and admixed with 50 ml each of water and tert-butyl methyl ether. The aqueous phase is removed and extracted with 40 ml of tert-butyl methyl ether. The combined organic phases are washed with 40 ml of brine, dried over sodium sulphate, filtered and concentrated to dryness. The title compound is obtained as a yellow oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.25 (3:1 EtOAc-heptane); Rt=4.34.

Aufarbeitung

  1. temperatureThe reaction solution is heated
  2. temperatureto reflux over 4 hours
  3. temperaturethe reaction solution is subsequently heated
  4. temperatureto reflux over a further 20 hours
  5. temperatureThe reaction solution is cooled
  6. customThe aqueous phase is removed
  7. extractionextracted with 40 ml of tert-butyl methyl ether
  8. washThe combined organic phases are washed with 40 ml of brine
  9. dry with materialdried over sodium sulphate
  10. filtrationfiltered
  11. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-5ef8d9917836464493ba001e9ae5eef9
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07842688B2

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