Acetic Acid → ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)aminomethyl]benzoate

HRID 355754

반응식

HRID 355754 반응식
[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:10]=1[CH:11]=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:18][CH2:19][C:20]1[CH:30]=[CH:29][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22][CH:21]=1.[BH4-].[Na+].C(O)(=O)C>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:10]=1[CH2:11][NH:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:29][CH:30]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 436161Ethyl 4-(aminomethyl)benzoateHCID 7330872-(Benzyloxy)-5-bromobenzaldehydeHCID 4311764Sodium borohydride

생성물 1

HCID 22675503ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)aminomethyl]benzoate

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

2-Benzyloxy-5-bromobenzaldehyde and ethyl 4-aminomethylbenzoate were heated together at 100° C. for 1 hour. The mixture was cooled, dissolved in ethanol (100 ml) and sodium borohydride (1.3 g) was added. The mixture was stirred for 18 hours at ambient temperature, acidified with acetic acid and water (200 ml) was added. The mixture was extracted with diethyl ether (4×100 ml), the extracts washed with saturated aqueous NaHCO3, dried (MgSO4), filtered and evaporated to give ethyl 4-[N-(2-benzyloxy-5-bromobenzyl)aminomethyl]benzoate which was purified by chromatography on silica gel eluting with CH2Cl2 then 5% ethyl acetate/CH2Cl2 (yield 11.4 g).

후처리

  1. temperatureThe mixture was cooled
  2. additionwas added
  3. extractionThe mixture was extracted with diethyl ether (4×100 ml)
  4. washthe extracts washed with saturated aqueous NaHCO3
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-ac2592b1d7e9403f99739f686d9d8a9c
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834468

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