Triethylamine → Methyl (R)-3-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-5-carboxylate

HRID 1193250ノート

反応式

HRID 1193250 の反応式
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C@H:8]2[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N(CC)CC)C>CO.CS(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:14]([O:13][C:12]([NH:11][C@H:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([C:12]([O:13][CH3:14])=[O:18])[CH:10]=2)[CH2:6][CH2:7]1)=[O:18])([CH3:17])([CH3:16])[CH3:15]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 59505686(R)-(6-Bromo-indan-1-yl)-carbamic acid tert-butyl ester

生成物 1

HCID 59505324Methyl (R)-3-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-5-carboxylate収率 76%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 679Dimethyl Sulfoxide溶媒HCID 887Methanol溶媒

実験手順

(R)-tert-Butyl 6-bromo-2,3-dihydro-1H-inden-1-ylcarbamate (15.0 g, 48.07 mmol, 1 eq) was dissolved in a mixture of methanol (200 ml) and DMSO (30 ml) and degassed for 30 min with argon, and palladium acetate (0.53 g, 2.40 mmol, 0.05 eq), 1,3-bis(diphenylphosphine)-propane (0.99 g, 2.40 mmol, 0.05 eq) and triethylamine (20 ml, 144.21 mmol, 3.0 eq) were added. In an autoclave, the reaction was sealed for 16 h at 75° C. at CO pressure (80 psi). Then the reaction mixture was dried under reduced pressure, and the residue was taken up in water (150 ml) and extracted with ethyl acetate (2×300 ml). The combined organic phases were washed with sat. NaCl solution (100 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 5% ethyl acetate in hexane) to give the desired product in the form of a white solid. Yield: 76% (10.6 g, 36.43 mmol).

後処理

  1. additionwere added
  2. customIn an autoclave, the reaction was sealed for 16 h at 75° C. at CO pressure (80 psi)
  3. customThen the reaction mixture was dried under reduced pressure
  4. extractionextracted with ethyl acetate (2×300 ml)
  5. washThe combined organic phases were washed with sat. NaCl solution (100 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by column chromatography (silica gel, 5% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-c2c42bc7818d4003a2a84fa7ee01c3cf
出典データセット
uspto-grants-2014_03
特許番号
US08680159B2

反応ノート

読み込み中…