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

HRID 268715ノート

反応式

HRID 268715 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 181649HOAt触媒HCID 6344Dichloromethane溶媒

実験手順

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

後処理

  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]

出典と根拠

ORDレコード
ord-eaf4a13f3987408dbfe953577a68dc63
出典データセット
uspto-grants-2008_11
特許番号
US07446103B2

反応ノート

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