Sodium Bicarbonate → Tert-butyl 3-(4-chloro-3-hydroxybenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

HRID 1176261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1176261
C([O:4][C:5]1[CH:6]=[C:7]([CH:43]=[CH:44][C:45]=1[Cl:46])[CH2:8][O:9][CH:10]1[CH:15]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])=[CH:18][CH:17]=2)[CH2:14][CH2:13][N:12]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:11]1)C=C.[BH4-].[Li+].C(=O)([O-])O.[Na+]>O1CCCC1.CC([O-])=O.CC([O-])=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd+2]>[Cl:46][C:45]1[CH:44]=[CH:43][C:7]([CH2:8][O:9][CH:10]2[CH:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[O:34][CH3:35])=[CH:18][CH:17]=3)[CH2:14][CH2:13][N:12]([C:36]([O:38][C:39]([CH3:41])([CH3:42])[CH3:40])=[O:37])[CH2:11]2)=[CH:6][C:5]=1[OH:4]

Komponenten

6

Edukt 3

HCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 68503445Tert-butyl 3-(3-allyloxy-4-chlorobenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy)phenyl}piperidine-1-carboxylate

Produkt 1

HCID 68506109Tert-butyl 3-(4-chloro-3-hydroxybenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 84538Bis(triphenylphosphinepalladium) acetateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The solution of 1.53 g of tert-butyl 3-(3-allyloxy-4-chlorobenzyloxy)-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 15 ml of tetrahydrofuran is admixed with stirring successively with 0.018 g of bis(triphenylphosphine)palladium(II) acetate and 0.053 g of lithium borohydride. The reaction mixture is stirred at room temperature over 16 hours, subsequently poured onto saturated aqueous sodium hydrogencarbonate solution and extracted with tert-butyl methyl ether (2×100 ml). The organic phases are washed with water (100 ml) and brine (100 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.45 (1:1 EtOAc-heptane); Rt=5.88.

Aufarbeitung

  1. extractionextracted with tert-butyl methyl ether (2×100 ml)
  2. washThe organic phases are washed with water (100 ml) and brine (100 ml)
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-fbdcb1788df7483b97565920d6aa35a0
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07842688B2

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