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Sodium Bicarbonate → 3,5-Dichlorobenzyl 4-(((tert-butoxycarbonyl)amino)methyl)-2-methylpiperidine-1-carboxylate

HRID 1480370
ノート
印刷プレビュー

反応式

HRID 1480370 の反応式
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][NH:12][CH:11]([CH3:15])[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[C:17](Cl)(=[O:28])[O:18][CH2:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:17]([O:18][CH2:19][C:20]2[CH:21]=[C:22]([Cl:27])[CH:23]=[C:24]([Cl:26])[CH:25]=2)=[O:28])[CH:11]([CH3:15])[CH2:10]1)=[O:16])([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 133055323,5-Dichlorobenzyl ChloroformateHCID 83918261tert-Butyl N-[(2-methylpiperidin-4-yl)methyl]carbamate

生成物 1

HCID 867226283,5-Dichlorobenzyl 4-(((tert-butoxycarbonyl)amino)methyl)-2-methylpiperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture comprising tert-butyl((2-methylpiperidin-4-yl)methyl)carbamate (step 2) (1.15 g, 5.04 mmol) and 3,5-dichlorobenzyl carbonochloridate (1.327 g, 5.54 mmol) in DCM (15 ml) was treated with aq. saturated sodium bicarbonate (0.504 ml, 5.04 mmol) and stirred at room temperature for 18 hours. The organic portion was separated and the aqueous phase extracted with DCM (2×10 ml). The combined organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure. Further purification by chromatography on silica, eluting in 0-20% 2M ammonia in MeOH in DCM afforded the title compound;

後処理

  1. customThe organic portion was separated
  2. extractionthe aqueous phase extracted with DCM (2×10 ml)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customFurther purification by chromatography on silica
  7. washeluting in 0-20% 2M ammonia in MeOH in DCM

出典と根拠

ORDレコード
ord-667d50e1f7f34a12b37e7adc8606d690
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409895B2

反応ノート

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