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Sodium Sulfate → Phenylmethyl [((3S)-1-{2-[6-(methyloxy)-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl]ethyl}-3-piperidinyl)methyl]carbamate

HRID 657127
ノート
印刷プレビュー

反応式

HRID 657127 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]=[CH:10][C:9](=[O:12])[N:8]([CH2:13][CH:14]=O)[C:7]=2[N:16]=1.[NH:17]1[CH2:22][CH2:21][CH2:20][C@@H:19]([CH2:23][NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:18]1.[O-]S([O-])(=O)=O.[Na+].[Na+].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:11]=[CH:10][C:9](=[O:12])[N:8]([CH2:13][CH2:14][N:17]3[CH2:22][CH2:21][CH2:20][C@@H:19]([CH2:23][NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:18]3)[C:7]=2[N:16]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 24436Sodium SulfateHCID 5049666Sodium triacetoxyborohydrideHCID 44828666(R)-benzyl piperidin-3-ylmethylcarbamateHCID 57815220(6-methoxy-3-oxopyrido(2,3-b)pyrazin-4(3H)-yl)acetaldehyde

生成物 1

HCID 86635363Phenylmethyl [((3S)-1-{2-[6-(methyloxy)-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl]ethyl}-3-piperidinyl)methyl]carbamate

試薬・触媒・溶媒 1

HCID 21226129Dichloromethane methanol溶媒

実験手順

[6-(Methyloxy)-3-oxopyrido[2,3-b]pyrazin-4(3H)-yl]acetaldehyde (for a preparation see Example 126(e)) (0.30 g, 1.36 mmol) was combined with phenylmethyl [(3R)-3-piperidinylmethyl]carbamate (for a preparation see Example 92(b)) (0.337 g, 1.36 mmol) in a 1:1 MeOH/DCM solution (30 mL). Excess Na2SO4 was added as a drying agent and the solution was stirred at ambient temperature for 16 h. NaBH(OAc)3 (0.86 g, 4.08 mmol) was added and the reaction was stirred an additional 2 h. The resulting solution was concentrated onto silica gel under vacuum and the crude residue was purified by column chromatography (silica gel) using a DCM/DCM-MeOH—NH4OH (90:10:1) gradient to yield the desired product as an off white solid (0.37 g, 61%).

後処理

  1. stirringthe reaction was stirred an additional 2 h
  2. concentrationThe resulting solution was concentrated onto silica gel under vacuum
  3. customthe crude residue was purified by column chromatography (silica gel)

出典と根拠

ORDレコード
ord-d82f8eee443d4d44b4753f0a7cab46e0
出典データセット
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08071592B2

反応ノート

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