(4-Phenyl-but-3-ynyl)-carbamic acid tert-butyl ester → cis-4-Phenyl-but-3-enylamine

HRID 6725

반응식

HRID 6725 반응식
C(OC(=O)[NH:7][CH2:8][CH2:9][C:10]#[C:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C)(C)C>N1C=CC=CC=1.[Pd]>[C:12]1(/[CH:11]=[CH:10]\[CH2:9][CH2:8][NH2:7])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

4

반응물 1

HCID 23544319(4-Phenyl-but-3-ynyl)-carbamic acid tert-butyl ester

생성물 1

HCID 12594566cis-4-Phenyl-but-3-enylamine

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 1049Pyridine용매

실험 절차

A suspension of palladium on barium sulfate (15 mg) was stirred for 15 min in 1 mL pyridine. (4-phenyl-but-3-ynyl)-carbamic acid tert-butyl ester (66 mg) was added and the solution was purged with hydrogen then stirred for 1 h under a hydrogen-filled balloon. The solution was diluted with ethyl acetate (10 ml) and washed 3 times with 1 N hydrochloric acid (10 ml). The ethyl acetate layer was dried over sodium sulfate and filtered. The filtrate was evaporated and the resulting residue (54 mg) is primarily cis-(4-phenyl-but-3-enyl)-carbamic acid tert-butyl ester along with (4-phenyl-but-3-ynyl)-carbamic acid tert-butyl ester, 4-phenylbutylamine, and trans-(4-phenyl-but-3-enyl)-carbamic acid tert-butyl ester. The combined minor products constitute ˜20% of the crude material. The tert-butoxycarbonyl group of the desired product was removed by Procedure P to give cis-4-phenyl-but-3-enylamine, which was used in subsequent transformations without further purification.

후처리

  1. customthe solution was purged with hydrogen
  2. additionfilled balloon
  3. additionThe solution was diluted with ethyl acetate (10 ml)
  4. washwashed 3 times with 1 N hydrochloric acid (10 ml)
  5. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated
  8. customThe tert-butoxycarbonyl group of the desired product was removed by Procedure P

출처 및 근거

ORD 기록
ord-1ba07cbda9804effb51403d0992a3d41
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084154B2

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