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Methanol → 4-(6-Cyclobutyl-5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzonitrile

HRID 1364159
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Reaktionsgleichung

Reaktionsgleichung von HRID 1364159
[N:1]1[N:2]([C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=2)[CH:3]=[C:4]2[CH2:10][CH2:9][NH:8][CH2:7][CH2:6][C:5]=12.[C:19]1(=O)[CH2:22][CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO>ClCCl.C(O)(=O)C>[CH:19]1([N:8]2[CH2:9][CH2:10][C:4]3=[CH:3][N:2]([C:11]4[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[CH:13][CH:12]=4)[N:1]=[C:5]3[CH2:6][CH2:7]2)[CH2:22][CH2:21][CH2:20]1
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Komponenten

7

Edukt 4

HCID 887MethanolHCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 669308824-(5,6,7,8-Tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzonitrile

Produkt 1

HCID 160489114-(6-Cyclobutyl-5,6,7,8-tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176
Acetic Acid
Katalysator
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-(5,6,7,8-Tetrahydropyrazolo[3,4-d]azepin-2(4H)-yl)benzonitrile (may be prepared as described in Description 11) (assumed 0.148 mmol) was dissolved in dichloromethane (2 ml) and acetic acid (2 drops). Cyclobutanone (17 μl, 0.22 mmol) and sodium triacetoxyborohydride (47 mg, 0.22 mmol) were added and the mixture stirred at room temperature for 1 hour. Methanol was added and the solution poured onto a 2 g SCX column which was eluted with methanol then 2M ammonia in methanol. The basic fractions were evaporated and the residue purified by flash chromatography eluting with 0-5% 2M ammonia in methanol/dichloromethane to give the title compound (E32).

Aufarbeitung

  1. additionthe solution poured onto a 2 g SCX column which
  2. washwas eluted with methanol
  3. customThe basic fractions were evaporated
  4. customthe residue purified by flash chromatography
  5. washeluting with 0-5% 2M ammonia in methanol/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-ffbfa2d8004d4afda1c853efcbbfd7bc
Quelldatensatz
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07888347B2

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