Sodium triacetoxyborohydride → benzyl 2,4-bis(benzyloxy)-6-(2-(dimethylamino)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-5-methylnicotinate

HRID 1481798Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1481798
[CH2:1]([O:8][C:9]1[N:24]=[C:23]([C:25]2[CH:33]=[CH:32][C:31]3[N:30]4[CH2:34][CH:35]([NH:37][CH3:38])[CH2:36][C:29]4=[CH:28][C:27]=3[CH:26]=2)[C:22]([CH3:39])=[C:21]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:48](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C=O>[CH2:1]([O:8][C:9]1[N:24]=[C:23]([C:25]2[CH:33]=[CH:32][C:31]3[N:30]4[CH2:34][CH:35]([N:37]([CH3:48])[CH3:38])[CH2:36][C:29]4=[CH:28][C:27]=3[CH:26]=2)[C:22]([CH3:39])=[C:21]([O:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 5049666Sodium triacetoxyborohydrideHCID 71284780benzyl 2,4-bis(benzyloxy)-5-methyl-6-(2-(methylamino)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)nicotinate

Produkt 1

HCID 71285017benzyl 2,4-bis(benzyloxy)-6-(2-(dimethylamino)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-5-methylnicotinateAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 712FormaldehydeKatalysatorHCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

The product from Example 415, Step 2 (31 mg, 0.05 mmol) was dissolved in 1,2-dichloroethane (1 mL). Aqueous 30% formaldehyde (1 drop, ˜0.2 mmol) was added to the mixture, followed by sodium triacetoxyborohydride (21 mg, 0.1 mmol). The mixture stirred at room temperature for 30 min. The mixture was loaded directly to silica gel, eluting with 0-8% MeOH in CH2Cl2 to afford product (25 mg, 78%). LC-MS 638.3 [M+H]+, RT 1.21 min.

Aufarbeitung

  1. washeluting with 0-8% MeOH in CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-c48e144b44054a00aec8f38fbe6bb46a
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409905B2

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