(4S)-4-Isobutyl-5,5-diphenyl-2-oxazolidinone → (S)-alpha-(Diphenylmethyl)-alpha-isobutyl-methylamine

HRID 1246386ノート

反応式

HRID 1246386 の反応式
C([C@H:5]1[C:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)O[C:7](=O)[NH:6]1)C(C)C.[H][H].[CH3:25]O.[CH3:27][C:28](O)=O>[Pd]>[C:10]1([CH:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C@@H:5]([NH:6][CH3:7])[CH:28]([CH3:27])[CH3:25])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

5

反応物 3

HCID 9904230(4S)-4-Isobutyl-5,5-diphenyl-2-oxazolidinoneHCID 10129899Acetic acid methanolHCID 178418361HCID 178418361、化合物

生成物 1

HCID 69593724(S)-alpha-(Diphenylmethyl)-alpha-isobutyl-methylamine収率 87%

試薬・触媒・溶媒 1

HCID 23938Palladium触媒

実験手順

A suspension of (S)-4-isobutyl-5,5-diphenyl-2-oxazolidinone 17 (7.6 g, 25.6 mmol) in MeOH/AcOH and a 10% Pd (282 mg, 2.6 mmol) on activated carbon was shaken for 93 h under 4–5 atm pressure of hydrogen at room temperature. The catalyst was filtered off over Hyflo Super Cell and solvents were evaporated under reduced pressure. The resulting residue was treated with HCl until all of the amine was converted to its HCl salt, stirred overnight at room temperature and diluted with water until partitioned occurred. The non-basic organics were extracted into diethyl ether (2×100 ml) and then the aqueous layer was made basic with NaOH pellets. Organics were then extracted into CH2Cl2 (5×100 ml) and the combined extracts were dried over MgSO4. Concentration gave the title product 18 (5.7 g, 87%) as a white amorphous solid. m.p. 46–48° C. [α]D25=−31.6° (c, 4.12 CHCl3). δH 0.86 (6H, dt, J=6.60 and 2.10 Hz, CH3), 1.00–1.50 (4H, m and broad s, CH2 and NH2), 1.66–1.86 (1H, m, CH), 3.61 (2H, broad s, CH—NH2 and CH—Ph2), 7.10–7.40 (10H, m, Ar—H). δC 21.8 and 24.7 (CH3), 25.5 (CH), 45.6 (CH2), 52.4 (CH—NH2), 61.6 (CH—Ph2), 126.9, 127.1, 128.8, 129.0, 129.2, 129.4, 143.8, 144.0 (Ar). Accurate mass (CI): Found 254.190200; Calculated for (MH+) C18H24N 254.190875 (2.7 ppm). νmax (cm−1): 3368 (N—H), 3057, 3027 (Ar C—H), 2951, 2932, 2909, 2867 (methyl and methylene C—H), 1595, 1494, 1450 (Ar C═C). m/e (CI) 254 (MH+, 100%).

後処理

  1. filtrationThe catalyst was filtered off over Hyflo Super Cell and solvents
  2. customwere evaporated under reduced pressure
  3. additionThe resulting residue was treated with HCl until all of the amine
  4. additiondiluted with water
  5. customuntil partitioned
  6. extractionThe non-basic organics were extracted into diethyl ether (2×100 ml)
  7. extractionOrganics were then extracted into CH2Cl2 (5×100 ml)
  8. dry with materialthe combined extracts were dried over MgSO4
  9. concentrationConcentration

出典と根拠

ORDレコード
ord-e8567b5ed5594b248e7f1eb9f611b93e
出典データセット
uspto-grants-2006_10
特許番号
US07126028B1

反応ノート

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