Formaldehyde → HCID 23627568, Verbindung

HRID 1423113

Reaktionsgleichung

Reaktionsgleichung von HRID 1423113
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:30](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:12][N:13]1[CH3:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 16725642(S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine

Produkt 1

HCID 23627568HCID 23627568, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (73 mg, 0.20 mmol) in CH2Cl2 (5 mL) was treated with a 37% aqueous formaldehyde solution (16 μL, 0.22 mmol) and stirred for 5 min after which time solid sodium triacetoxyborohydride (64 mg, 0.30 mmol) was added. The suspension was then stirred for 3 hr then quenched with a saturated aqueous NaHCO3 solution (2 mL). The organic component was separated, dried over MgSO4, filtered, and evaporated to an oil which was purified by silica gel flash chromatography with 5% MeOH/CH2Cl2 as eluant to afford the title compound as a burgundy oil (69 mg, 91%). 1H NMR (CDCl3) 7.33-7.20 (m, 5H), 6.72 (d, J=8.6, 1H), 6.35 (d, J=2.9, 1H), 6.30 (dd, J=8.6, 2.9, 1H), 4.62-4.59 (m, 1H), 3.76 (s, 3H), 3.32-3.22 (m, 2H), 3.13-3.02 (m, 3H), 2.67-2.60 (m, 4H), 2.57 (s, 3H), 1.85-1.77 (m, 6H), 1.61-1.54 (m, 2H). 13C NMR 148.4, 146.1, 144.5, 139.0 (CH), 129.5 (CH), 128.6, 126.4 (CH), 113.2 (CH), 107.8 (CH), 106.2 (CH), 80.4 (CH), 63.7 (CH), 56.8 (CH3), 55.1 (CH2), 55.0 (CH2), 50.2 (CH2), 42.9 (CH3), 36.3 (CH2), 33.0 (CH2), 24.2 (CH2). LC/MS (Method A) 5.10 min, [M+1]+ 381.

Aufarbeitung

  1. additionwas added
  2. customthen quenched with a saturated aqueous NaHCO3 solution (2 mL)
  3. customThe organic component was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to an oil which
  7. customwas purified by silica gel flash chromatography with 5% MeOH/CH2Cl2 as eluant

Quellen und Nachweise

ORD-Eintrag
ord-400df85a0cf24a66810af24cd8b0040f
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927546B2

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