5-Aminovaleric acid → 4-(2-Oxopiperidinomethyl)-nitrobenzene

HRID 1373128

반응식

HRID 1373128 반응식
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O.C([BH3-])#N.[Na+].Cl>CO.O>[O:19]=[C:17]1[CH2:16][CH2:15][CH2:14][CH2:13][N:12]1[CH2:8][C:7]1[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

참가 물질

7

반응물 4

HCID 1385-Aminovaleric acidHCID 313Hydrochloric AcidHCID 5414-NitrobenzaldehydeHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 180056574-(2-Oxopiperidinomethyl)-nitrobenzene

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

6.4 g (42 mmol) of 4-nitrobenzaldehyde are dissolved in 150 ml of methanol and combined with 4.9 g (42 mmol) of 5-aminovaleric acid and 1.8 g (29 mmol) of sodium cyanoborohydride. The mixture is stirred for 18 hours at ambient temperature and then carefully mixed with 20 ml of conc. hydrochloric acid. The solvent is eliminated in vacuo, the residue is taken up in water and extracted with dichloromethane. The residue obtained after evaporation is chromatographed on silica gel (dichloromethane/methanol, 4:1). A mixture of methyl 5-(4-nitrobenzylamino)-pentanoate and 4-(2-oxopiperidinomethyl)-nitrobenzene is obtained which is dissolved in 100 methanol and combined with 50 ml of 1 N sodium hydroxide solution. The mixture is stirred for one hour at ambient temperature, 50 ml of 1 N hydrochloric acid are added and the reaction solution is evaporated down to 100 ml. The aqueous phase thus obtained is extracted with dichloromethane. The combined organic phases are dried over sodium sulphate and evaporated to dryness.

후처리

  1. extractionextracted with dichloromethane
  2. customThe residue obtained
  3. customafter evaporation
  4. customis chromatographed on silica gel (dichloromethane/methanol, 4:1)
  5. additionA mixture of methyl 5-(4-nitrobenzylamino)-pentanoate

출처 및 근거

ORD 기록
ord-3ee0601106844b04b779bf038b6cdf6e
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07160901B2

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