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Formaldehyde → (R)-4-((1-methylpiperidin-2-yl)methoxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

HRID 60305
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HRID 60305 반응식
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:7][O:8][C:9]1[C:17]2[C:16]3[CH:18]=[C:19]([C:22]#[N:23])[N:20]=[CH:21][C:15]=3[N:14]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:13]=2[N:12]=[CH:11][CH:10]=1.C=O.[C:34](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C.O.C(=O)(O)[O-].[Na+].C(Cl)Cl>[CH3:34][N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:7][O:8][C:9]1[C:17]2[C:16]3[CH:18]=[C:19]([C:22]#[N:23])[N:20]=[CH:21][C:15]=3[N:14]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:13]=2[N:12]=[CH:11][CH:10]=1
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참가 물질

8

반응물 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58365030(R)-4-(piperidin-2-ylmethoxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

생성물 1

HCID 67249073(R)-4-((1-methylpiperidin-2-yl)methoxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile

시약·촉매·용매 4

HCID 962
Water
용매
HCID 6342Acetonitrile용매
HCID 6344Dichloromethane용매
HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of (R)-4-(piperidin-2-ylmethoxy)-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (220 mg, 0.50 mmol) in acetonitrile (2.2 mL) and water (0.45 mL) was added Formalin (41 uL, 1.5 mmol) followed by sodium triacetoxyborohydride (210 mg, 1.0 mmol), and the reaction mixture was stirred at ambient temperature for 20 minutes. The mixture diluted with saturated aqueous sodium bicarbonate solution (50 mL) and methylene chloride (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, concentrated in vacuo, and purified flash chromatography (silica, 4 g, ISCO, 1-20% methanol in methylene chloride) to afford the title compound as a yellow solid, which was used in the next step without any further purification (197 mg, 87%).

후처리

  1. customThe organic layer was separated
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custompurified flash chromatography (silica, 4 g, ISCO, 1-20% methanol in methylene chloride)

출처 및 근거

ORD 기록
ord-7364bca3d9bd48369f0bdd677da07ff0
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09440976B2

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