1,2-Dichloroethane → N-t-Butoxycarbonyl-5-[(pyrrolidin-1-yl)carbonyl]isoindoline

HRID 268715노트

반응식

HRID 268715 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]([OH:19])=O)[CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.[CH2:24]([N:26](CC)[CH2:27][CH3:28])[CH3:25].N1CCCC1>C(Cl)Cl.C1C=NC2N(O)N=NC=2C=1>[C:1]([O:5][C:6]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]([N:26]3[CH2:27][CH2:28][CH2:25][CH2:24]3)=[O:19])[CH:14]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

7

반응물 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 31268PyrrolidineHCID 164501432-(tert-Butoxycarbonyl)-2,3-dihydro-1H-isoindole-5-carboxylic acid

생성물 1

HCID 17986289N-t-Butoxycarbonyl-5-[(pyrrolidin-1-yl)carbonyl]isoindoline

시약·촉매·용매 2

HCID 181649HOAt촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of N-t-butoxycarbonyl-5-carboxyisoindoline (D13) (300 mg), EDC (440 mg), HOAT (10 mg), triethylamine (0.4 ml) and pyrrolidine (0.11 ml) in DCM (10 ml) was stirred overnight and then evaporated. The residue was redissolved in EtOAc (10 ml), washed with saturated NaHCO3 solution (10 ml), water (10 ml), brine (10 ml), dried (MgSO4) and evaporated. The residue was chromatographed on a silica gel flash column [step gradient 70-90% EtOAc in light petroleum 40-60] to give the tiUe compound (D17) (314 mg). MS electrospray (+ion) 317 (MH+). 1H NMR δ (CDCl3): 7.42 (2H, m), 7.27 (1H, m), 4.70 (2H, m), 4.67 (2H, m), 3.65 (2H, m), 3.42 (2H, m), 1.92 (4H, m), 1.52

후처리

  1. customevaporated
  2. dissolutionThe residue was redissolved in EtOAc (10 ml)
  3. washwashed with saturated NaHCO3 solution (10 ml), water (10 ml), brine (10 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was chromatographed on a silica gel flash column [step gradient 70-90% EtOAc in light petroleum 40-60]

출처 및 근거

ORD 기록
ord-eaf4a13f3987408dbfe953577a68dc63
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446103B2

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