Hydrochloric Acid → HCID 178501122, 화합물

HRID 538074

반응식

HRID 538074 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH:11]=O)([O-:3])=[O:2].Cl.[CH3:14][O:15][C:16]([C@H:18]1[CH2:23][CH2:22][C@H:21]([CH2:24][NH2:25])[CH2:20][CH2:19]1)=[O:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>C(Cl)Cl>[CH3:14][O:15][C:16]([C@H:18]1[CH2:23][CH2:22][C@H:21]([CH2:24][NH:25][CH2:11][CH2:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:20][CH2:19]1)=[O:17]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 108447642-NitrobenzeneacetaldehydeHCID 178501119HCID 178501119, 화합물

생성물 1

HCID 178501122HCID 178501122, 화합물수율 27%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of (2-Nitro-phenyl)-acetaldehyde (1 g, 5.98 mmol), trans-4-Aminomethyl cyclohexanecarboxylic acid methyl ester hydrogen chloride salt (1.37 g, 6.58 mmol) and TEA (0.92 mL, 6.58 mmol) in dry DCM was stirred at room temperature for 2.5 h. Sodium triacetoxy borohydride (2.53 g, 11.96 mmol) was added and the mixture stirred at room temperature for 25 min. Then (2N) HCl was added until acidic pH and the aqueous layer extracted with DCM. The organic layer was washed with a saturated solution of NaHCO3 and dried over Na2SO4 anhydrous and then evaporated to afford crude product. Finally, the crude product was purified by flash chromatography on silica (ETP/EtOAc 9/1→0/1) to obtain the titled compound (0.51 g, yield: 27%).

후처리

  1. extractionthe aqueous layer extracted with DCM
  2. washThe organic layer was washed with a saturated solution of NaHCO3
  3. dry with materialdried over Na2SO4 anhydrous
  4. customevaporated
  5. customto afford crude product
  6. customFinally, the crude product was purified by flash chromatography on silica (ETP/EtOAc 9/1→0/1)

출처 및 근거

ORD 기록
ord-46d4c2e571d7477b818f60875b53b2d1
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865704B2

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