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

HRID 403596ノート

反応式

HRID 403596 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-bb3c184400d74032900e677a39c26619
出典データセット
uspto-grants-2014_06
特許番号
US08748444B2

反応ノート

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