(2S,3S,alphaS)-t-Butyl 3-(N-allyl-alpha-methylbenzylamino)-2-hydroxy-3-phenylpropionate → (2S,4S,5S,alphaS)-2-Ethyl-3-(alpha-methylbenzyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid t-butyl ester

HRID 1637047ノート

反応式

HRID 1637047 の反応式
[CH2:1]([N:4]([C@@H:21]([CH3:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C@@H:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C@H:6]([OH:14])[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:2]=[CH2:3]>C1(C)C=CC=CC=1.[Rh]Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:10]([O:9][C:7]([C@H:6]1[O:14][C@@H:1]([CH2:2][CH3:3])[N:4]([C@@H:21]([CH3:28])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@H:5]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:8])([CH3:13])([CH3:12])[CH3:11]

参加物

4

反応物 1

HCID 86755227(2S,3S,alphaS)-t-Butyl 3-(N-allyl-alpha-methylbenzylamino)-2-hydroxy-3-phenylpropionate

生成物 1

HCID 86755235(2S,4S,5S,alphaS)-2-Ethyl-3-(alpha-methylbenzyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid t-butyl ester収率 83%

試薬・触媒・溶媒 2

HCID 178479813HCID 178479813、化合物触媒HCID 1140Toluene溶媒2 回

実験手順

To a solution of compound (27) from Example 12 (1.039 g, 2.73 mmol) in anhydrous toluene (25 ml) was added tris(triphenylphosphine) rhodium(I) chloride (126 mg, 5 mol %). This solution was refluxed for 4 hours whereafter the toluene was removed under reduced pressure. The residue was treated with diethyl ether, precipitating the catalyst, and the solution was passed through alumina grade 5. After removal of the solvent under reduced pressure, the resulting oil was purified by flash chromatography on silica gel [ethyl acetate/petroleum ether (1:19)] affording the title compound (Rf 0.40) as a colourless oil (0.86 g, 83%). δH (300 MHz; CDCl3) 7.33-7.18 (10H, m, Ph), 4.48 (1H, t, NCHO), 4.38 (1H, d, J=8.0, PhCHCH), 4.21 (1H, d, J=8.0, PhCHCH), 4.01 (1H, q, J=6.9, PhCHCH3), 1.91 (2H, m, CHCH2CH3), 1.27 (3H, d, J=6.9, PhCHCH3), 1.15 (3H, t, J=7.5, CHCH2CH3), 0.99 (9H, s, (CH3)3C).

後処理

  1. customwas removed under reduced pressure
  2. additionThe residue was treated with diethyl ether
  3. customprecipitating the catalyst
  4. customAfter removal of the solvent under reduced pressure
  5. customthe resulting oil was purified by flash chromatography on silica gel [ethyl acetate/petroleum ether (1:19)]

出典と根拠

ORDレコード
ord-ad151db2dfb64c179edb4f15a00b19e2
出典データセット
uspto-grants-2000_03
特許番号
US06037498

反応ノート

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