(4S)-4-Methyl-5,5-diphenyl-1,3-oxazolidin-2-one → (S)-(-)-1,1-Diphenyl-2-aminopropane

HRID 1246382노트

반응식

HRID 1246382 반응식
[CH3:1][C@H:2]1[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)OC(=O)[NH:3]1.[H][H]>CO.CC(O)=O.[Pd]>[NH2:3][C@@H:2]([CH3:1])[CH:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

5

반응물 2

HCID 10220643(4S)-4-Methyl-5,5-diphenyl-1,3-oxazolidin-2-oneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 10198226(S)-(-)-1,1-Diphenyl-2-aminopropane수율 65%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 10129899Acetic acid methanol용매

실험 절차

A suspension of (S)-4-methyl-5,5-diphenyl-2-oxazolidinone (11) (3.52 g, 13.90 mmol) in MeOH/AcOH and a 10% Pd (148 mg, 1.39 mmol) on activated carbon was shaken for 45 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 (2M, 100 ml), stirred overnight at room temperature, made basic with NaOH pellets, and saturated with K2CO3. The organics were then extracted into diethyl ether (3×100 ml), dried over MgSO4/K2CO3 and concentrated under reduced pressure to obtain a crude product. Impurities were washed with AcOEt over silica gel by means of dry-flash column chromatography, and then further elution with a mixture of MeOH and AcOEt, ranging from 5% up to 30%, gave the title compound (12) (1.90 g, 65%) as a white solid. m.p. 76–77° C. [α]D25=−19.32 (c, 0.10765 in CHCl3). δH 1.04 (3H, d, 3J=6.30 Hz, CH3), 1.31 (2H, broad s, NH2), 3.55 (1H, d, J=9.90 Hz, CH—Ph2), 3.73 (1H, dq, 3J=6.30 and 10.20 Hz, CH—NH2), 7.10–7.40 (10H, m, Ar—H). δC 22.4 (CH3), 50.3 (CH—NH2), 62.4 (CH—Ph2), 126.5, 126.8, 128.2, 128.5, 128.7 and 129.0 (o-, m- and p-Ar), 143.3 and 143.7 (α-Ar). Anal. Calcld for C15H17NO: C 85.26; H 8.11; N 6.63. Found: C 85.10; H 8.08; N 6.36. ir 3343 (NH2). m/e (CI—NH3) 212 (MH+, 100%).

후처리

  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 (2M, 100 ml)
  4. extractionThe organics were then extracted into diethyl ether (3×100 ml)
  5. dry with materialdried over MgSO4/K2CO3
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a crude product
  8. washImpurities were washed with AcOEt over silica gel by means of dry-flash column chromatography
  9. washfurther elution
  10. additionwith a mixture of MeOH and AcOEt

출처 및 근거

ORD 기록
ord-5d1e1e9619d044e7936d463b962acd5e
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07126028B1

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