Potassium Carbonate → 1-((S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-ylamino)-3-phenylhex-5-en-3-ol

HRID 403596

반응식

HRID 403596 반응식
[Si:1]([O:8][C:9]([CH3:14])([CH3:13])[C@@H:10]([NH2:12])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl[CH2:16][CH2:17][C:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([OH:22])[CH2:19][CH:20]=[CH2:21].C([O-])([O-])=O.[K+].[K+]>CC#N>[Si:1]([O:8][C:9]([CH3:13])([CH3:14])[C@@H:10]([NH:12][CH2:16][CH2:17][C:18]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([OH:22])[CH2:19][CH:20]=[CH2:21])[CH3:11])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 159334751-Chloro-3-phenylhex-5-en-3-olHCID 58485259(S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-amine

생성물 1

HCID 584852601-((S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-ylamino)-3-phenylhex-5-en-3-ol수율 3.3%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of (S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-amine (6 g, 27.6 mmol), 1-chloro-3-phenylhex-5-en-3-ol (4.83 g, 23 mmol) and K2CO3 (15 g, 100 mmol) in CH3CN (100 mL) was stirred and heated to reflux overnight. The solid was filtered, and the filtrate was concentrated to give the crude product which was purified by column chromatography to afford 1-((S)-3-(tert-butyldimethylsilyloxy)-3-methylbutan-2-ylamino)-3-phenylhex-5-en-3-ol (300 mg, 3%). 1H NMR (CDCl3): 0.00 (s, 6H), 0.73 (s, 9H), 1.02 (s, 3H), 1.12 (d, 3H), 1.21 (s, 3H), 1.92 (m, 2H), 2.30 (m, 4H), 2.49 (m, 3H), 2.96 (m, 2H), 4.92 (m, 3H), 5.45 (m, 2H), 7.11 (m, 1H), 7.21 (m, 2H), 7.26 (m, 2H).

후처리

  1. temperatureheated
  2. temperatureto reflux overnight
  3. filtrationThe solid was filtered
  4. concentrationthe filtrate was concentrated
  5. customto give the crude product which
  6. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-bb3c184400d74032900e677a39c26619
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748444B2

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