Formaldehyde → HCID 23627568, Verbindung

HRID 1171903Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1171903
[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, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (Example 2) (73 mg, 0.2 mmol) in CH2Cl2 (5 mL) was treated with a 37% aqueous formaldehyde solution (16.4 uL, 0.22 mmol) and stirred for 5 min after which time solid sodium triacetoxyborohydride (64 mg, 0.3 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 product as a burgundy oil (69 mg, 91%). 1H NMR (CDCl3) 1.54-1.61 (m, 2H), 1.77-1.85 (m, 6H), 2.57 (s, 3H), 2.60-2.67 (m, 3H), 3.02-3.13 (m, 3H), 3.22-3.32 (m, 2H), 3.76 (s, 3H), 4.59-4.62 (m, 1H), 3.76 (s, 3 H), 4.59-4.62 (m, 1H), 6.30 (dd, J=8.6, 2.9, 1H), 6.35 (d, J=8.6, 1H), 7.20-7.33 (m, 5H). 13C NMR 24.2 (CH2), 33.0 (CH2), 36.3 (CH2), 42.9(CH3), 50.2 (CH2), 55.0 (CH2), 55.1 (CH2), 56.8 (CH3), 63.7 (CH), 80.4 (CH), 106.2 (CH), 107.8(CH), 113.2(CH), 126.4 (CH) 128.6, 129.5 (CH), 139.0 (CH), 144.5, 146.1, 148.4. LC/MS 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-403e95c19c0a401ebe3bb4105e163d15
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829713B2

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