4-(4-Fluorophenyl)piperidine → 1-Allyl-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidine

HRID 279215Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 279215
[CH2:1]([N:4]1[CH2:8][CH:7]([CH:9]2[CH2:11][CH2:10]2)[CH:6]([CH:12]=O)[CH2:5]1)[CH:2]=[CH2:3].[F:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)=[CH:17][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH2:1]([N:4]1[CH2:8][CH:7]([CH:9]2[CH2:11][CH2:10]2)[CH:6]([CH2:12][N:24]2[CH2:25][CH2:26][CH:21]([C:18]3[CH:17]=[CH:16][C:15]([F:14])=[CH:20][CH:19]=3)[CH2:22][CH2:23]2)[CH2:5]1)[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 27591364-(4-Fluorophenyl)piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 226244751-allyl-3-(RS)-formyl-4-(SR)-(cyclopropyl)pyrrolidine

Produkt 1

HCID 226244721-Allyl-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-(cyclopropyl)pyrrolidineAusbeute 61,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of 1.8 g (10 mmol) of 1-allyl-3-(RS)-formyl-4-(SR)-(cyclopropyl)pyrrolidine and 2.68 g (15 mmol) of 4-(4-fluorophenyl)piperidine in 30 mL of dichloroethane at rt was added portionwise 6.36 g (30 mmol) of sodiumtriacetoxyborohydride. After stirring for 3 h at rt, the reaction mixture was partitioned between CH2Cl2 and sat'd K2CO3. The organic fraction was dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chomatography (silica, ethyl acetate:hexanes, 1:3) to give 2.1 g of the title compound.

Aufarbeitung

  1. customthe reaction mixture was partitioned between CH2Cl2
  2. dry with materialThe organic fraction was dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chomatography (silica, ethyl acetate:hexanes, 1:3)

Quellen und Nachweise

ORD-Eintrag
ord-f2f93066fb644903859a466072cb27f8
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362201B1

Notizen zur Reaktion

Wird geladen…