N,N,N',N'-Tetramethylethylenediamine → Spiro[cyclohexane-1,3'-indolin]-2'-one

HRID 6997

반응식

HRID 6997 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].C([Li])CCC.CN(C)CCN(C)C.I[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]I.[Cl-].[NH4+]>O1CCCC1.CCOC(C)=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[C:2]1=[O:10]

참가 물질

8

반응물 5

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 123541,5-DiiodopentaneHCID 25517Ammonium ChlorideHCID 321710OxindoleHCID 178418339Butyllithium

생성물 1

HCID 12888301Spiro[cyclohexane-1,3'-indolin]-2'-one수율 69.6%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of oxindole (25 g, 0.19 mol) in anhydrous tetrahydrofuran (800 cm3) was cooled to −20° C., then n-butyllithium (2.5M in hexanes, 152 cm3, 0.38 mol) was added slowly followed by N,N,N′,N′-tetramethylethylenediamine (51 cm3, 0.38 mol,). After 15 min. 1,5-diiodopentane (174 g, 0.54 mol) was added slowly and the mixture was allowed to warm to room temperature. After stirring for 16 h. saturated aqueous ammonium chloride solution (1 L) and EtOAc (1 L) were added. After 15 min. the layers were separated and the aqueous phase was extracted EtOAc (×2). The combined organic layers were extracted with hydrochloric acid (1N), then washed with brine (500 cm3), dried (MgSO4), and concentrated to obtain an oil. The oil was triturated with hexane (200 cm3) and benzene (20 cm3). The precipitate was collected and dried in vacuo to obtain the subtitled compound (26.3 g, 69.6%) as colorless crystals: mp 110–114° C.; 1H NMR (DMSO-d6) δ 1.67 (m, 10H), 6.84 (d, 1H, J=8 Hz) 6.94 (t, 1H, J=8 Hz), 7.17 (t, 1H, J=8 Hz), 7.44 (d, 1H, J=8 Hz), 10.3 (s, 1H).

후처리

  1. additionwere added
  2. customAfter 15 min. the layers were separated
  3. extractionthe aqueous phase was extracted EtOAc (×2)
  4. extractionThe combined organic layers were extracted with hydrochloric acid (1N)
  5. washwashed with brine (500 cm3)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customto obtain an oil
  9. customThe oil was triturated with hexane (200 cm3) and benzene (20 cm3)
  10. customThe precipitate was collected
  11. customdried in vacuo

출처 및 근거

ORD 기록
ord-d24153be9c474bb28c86121b580a0c0d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084168B2

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