1,2-Dichloroethane → HCID 66970642, Verbindung

HRID 1361518

Reaktionsgleichung

Reaktionsgleichung von HRID 1361518
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:16][CH3:17])=[C:6]([C:8]2([O:14][CH3:15])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=1.[BH-](O[C:28]([CH3:30])=O)(OC(C)=O)OC(C)=O.[Na+].Cl[CH2:33][CH2:34]Cl>>[C@H:34]12[CH2:33][C@H:7]([CH:2]=[CH:3]1)[CH2:6][C@@H:28]2[CH2:30][N:11]1[CH2:10][CH2:9][C:8]([C:6]2[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[O:16][CH3:17])([O:14][CH3:15])[CH2:13][CH2:12]1

Komponenten

4

Edukt 3

HCID 111,2-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 587722974-(5-Chloro-2-methoxyphenyl)-4-methoxypiperidine

Produkt 1

HCID 66970642HCID 66970642, Verbindung

Versuchsvorschrift

4-(5-Chloro-2-methoxyphenyl)-4-methoxypiperidine 5d (51 mg, 0.2 mmol) was dissolved in 1,2-dichloroethane (1.5 mL) and treated with (S,S,S)-norbornene carboxaldehyde (24 mg, 0.2 mmol, 1.0 eq), followed by the addition of NaBH(OAc)3 (65 mg, 0.3 mmol, 1.5 eq). The reaction was allowed to stir at room temperature for 1 h, quenched with methanol (1 mL) and allowed to stir for another 30 min (until gas evolution stopped). The crude reaction mixture was purified by HPLC (10-99 CH3CN gradient, 0.05% TFA) to provide the desired product 1-(((1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl)methyl)-4-(5-chloro-2-methoxyphenyl)-4-methoxypiperidine (compound no. 140) as the TFA salt. LC/MS (RP-C18, 10-99% CH3CN/0.05% TFA gradient over 5 min) m/z 362.2 [M+H]+, retention time 2.53 min.

Aufarbeitung

  1. customquenched with methanol (1 mL)
  2. stirringto stir for another 30 min (until gas evolution stopped)
  3. customThe crude reaction mixture
  4. customwas purified by HPLC (10-99 CH3CN gradient, 0.05% TFA)

Quellen und Nachweise

ORD-Eintrag
ord-1aa2781b4e1941ba860470fe5eea490a
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07880007B2

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