Propanal → 4-But-3-enyl-5-ethyl-2,2-diphenyl-oxazolidine-4-carboxylic acid tert-butyl ester

HRID 579522노트

반응식

HRID 579522 반응식
[C:1]([O:5][C:6](=[O:26])[CH:7]([N:12]=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:8][CH2:9][CH:10]=[CH2:11])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl-].C([Al+]CC)C.[CH:43](=[O:46])[CH2:44][CH3:45]>C1COCC1>[C:1]([O:5][C:6]([C:7]1([CH2:8][CH2:9][CH:10]=[CH2:11])[CH:43]([CH2:44][CH3:45])[O:46][C:13]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:12]1)=[O:26])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 527PropanalHCID 2724254Sodium bis(trimethylsilyl)amideHCID 160669741,1-Dimethylethyl 2-[(diphenylmethylene)amino]-5-hexenoateHCID 16686102Diethyl aluminum chloride

생성물 1

HCID 668332184-But-3-enyl-5-ethyl-2,2-diphenyl-oxazolidine-4-carboxylic acid tert-butyl ester수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

While under a nitrogen atmosphere, a stirred solution of 2-(benzhydrylidene-amino)-hex-5-enoic acid tert-butyl ester (350 mg, 1 mmol) in THF (5 mL, 0.2 M) was cooled to −78° C. and carefully treated with sodium bis(trimethylsilyl)amide (2 mL, 1 M, 2 equiv). After stirring 30 min, diethyl aluminum chloride (2.4 mL, 1 M, 2.4 equiv) was added and the reaction mixture was stirred an additional 30 min. Propionaldehyde (94 μl, 1.25 mmol, 1.25 eq) was added to the solution and the cooling bath was removed. After stirring overnight the reaction mixture was cooled to 0° C. and quenched with saturated NH4Cl. The resulting solution was diluted with ethyl acetate and washed successively with water and saturated potassium sodium tartrate, dried over MgSO4, filtered and concentrated. Purification by MPLC (1-40% ethyl acetate in heptane) gave 4-but-3-enyl-5-ethyl-2,2-diphenyl-oxazolidine-4-carboxylic acid tert-butyl ester (349 mg, 0.86 mmol, 86%).

후처리

  1. stirringthe reaction mixture was stirred an additional 30 min
  2. customthe cooling bath was removed
  3. stirringAfter stirring overnight the reaction mixture
  4. customquenched with saturated NH4Cl
  5. additionThe resulting solution was diluted with ethyl acetate
  6. washwashed successively with water and saturated potassium sodium tartrate
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by MPLC (1-40% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-c5ae4b94a0f84a3eb884600a758f3701
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040703B2

반응 노트

불러오는 중…