(4S)-5,5-Diphenyl-4-(propan-2-yl)-1,3-oxazolidin-2-one → (S)-2-Amino-3-methyl-1,1-diphenylbutane

HRID 1246377

反応式

HRID 1246377 の反応式
[CH:1]([C@H:4]1[C:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)OC(=O)[NH:5]1)([CH3:3])[CH3:2].[H][H]>CO.CC(O)=O.[Pd]>[NH2:5][C@@H:4]([CH:1]([CH3:3])[CH3:2])[CH:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 2

HCID 9838646(4S)-5,5-Diphenyl-4-(propan-2-yl)-1,3-oxazolidin-2-oneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 9794746(S)-2-Amino-3-methyl-1,1-diphenylbutane収率 72.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 10129899Acetic acid methanol溶媒

実験手順

A solution of (S)-4-isopropyl-5,5-diphenyl-2-oxazolidinone (3) (2.9 g, 10.31 mmol) in MeOH/AcOH and a 10% Pd (435 mg, 4.09 mmol) on activated carbon was shaken for 68 h under 4–5 atm pressure of hydrogen at room temperature. The catalyst was filtered off over Hyflo Super Cell and organic solvents were evaporated under reduced pressure. The resulting residue was treated with HCl (2.0 M, 50 ml), stirred for 2 h at room temperature, made basic with NaOH pellets, and saturated with K2CO3 and NaCl. Organic compounds were then extracted into AcOEt (3×100 ml), dried over MgSO4/K2CO3 and concentrated under reduced pressure to obtain a crude product. Re-crystallisation from petroleum ether gave the title compound (4) (1.79 g, 72%) as a light-brown solid. m.p. 71–72° C. [α]D25=−4.19° (c, 0.1097 in CHCl3). δH 0.78 (3H, d, 3J=6.60 Hz, CH3), 0.91 (3H, d, 3J=7.20 Hz, CH3), 1.26 (2H, broad s, NH2), 1.62 (1H, ds, CHMe2), 3.45 (1H, dd, 3J=10.5 and 2.40 Hz, CH—NH2), 3.70 (1H, d, 3J=10.5 Hz, CH—Ph2), 7.00–7.40 (10H, m, Ar—H). δC 14.2 and 21.5 (CH3), 28.9 (CH—Me2), 58.1 and 58.9 (CH—NH2 and CH—Ph2), 126.5, 126.7, 128.2, 128.5, 128.8 and 129.0 (o-, m- and p-Ar), 143.5 (2×α-Ar). Anal. Calcld for C17H21N: C 85.30; H 8.84; N 5.85. Found: C 85.12; H 8.91; N 5.96. ir 3361 (NH2). m/e (CI—CH4) 240 (MH+, 8%), 72 (100%).

後処理

  1. filtrationThe catalyst was filtered off over Hyflo Super Cell and organic solvents
  2. customwere evaporated under reduced pressure
  3. additionThe resulting residue was treated with HCl (2.0 M, 50 ml)
  4. extractionOrganic compounds were then extracted into AcOEt (3×100 ml)
  5. dry with materialdried over MgSO4/K2CO3
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a crude product

出典と根拠

ORDレコード
ord-b438dce7dcba4ca88085423ad3aa4d3b
出典データセット
uspto-grants-2006_10
特許番号
US07126028B1

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