Homoallyl bromide → 1,1-Dimethylethyl 2-[(diphenylmethylene)amino]-5-hexenoate

HRID 579521

반응식

HRID 579521 반응식
[C:1]([O:5][C:6](=[O:22])[CH2:7][N:8]=[C:9]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:34][CH2:35][CH:36]=[CH2:37]>C1COCC1>[C:1]([O:5][C:6](=[O:22])[CH:7]([N:8]=[C:9]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[CH2:37][CH2:36][CH:35]=[CH2:34])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 21241Homoallyl bromideHCID 688171N-(Diphenylmethylene)glycine tert-butyl esterHCID 2724254Sodium bis(trimethylsilyl)amide

생성물 1

HCID 160669741,1-Dimethylethyl 2-[(diphenylmethylene)amino]-5-hexenoate수율 94.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

While under a nitrogen atmosphere a stirred solution of (benzhydrylidene-amino)-acetic acid tert-butyl ester (5 g, 16.9 mmol) in THF (80 mL, 0.2 M) was carefully treated with sodium bis(trimethylsilyl)amide (18.6 mL, 1.0 M, 1.1 equiv) at −78° C. After stirring for 30 min, 4-bromo-but-1-ene (2.1 mL, 20.3 mmol, 1.2 equiv) was slowly added. The cooling bath was removed and the reaction mixture gradually warmed to room temperature and stirred for overnight. The solution was cooled to 0° C. and quenched with water. The resulting solution was diluted with ethyl acetate and washed successively with water and saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. Purification by MPLC (1-25% ethyl acetate in heptane) gave 2-(benzhydrylidene-amino)-hex-5-enoic acid tert-butyl ester as colorless oil (5.6 g, 15.9 mmol, 94%).

후처리

  1. customThe cooling bath was removed
  2. stirringstirred for overnight
  3. temperatureThe solution was cooled to 0° C.
  4. customquenched with water
  5. additionThe resulting solution was diluted with ethyl acetate
  6. washwashed successively with water and saturated aqueous NaCl
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by MPLC (1-25% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-1a24c120d9d042f78e7613297ca80e5d
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040703B2

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