Benzyl Alcohol → 1-Tert-butyloxycarbonyl-trans-3-benzyloxycarbonylamino-4-(2-pyridyl)pyrrolidine

HRID 398399ノート

反応式

HRID 398399 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C@H:10](C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:24]([CH:28](C)C)C(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:38])C=CC=CC=1.[CH2:48]([OH:55])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1>C1(C)C=CC=CC=1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C@H:10]([NH:24][C:28]([O:55][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[O:38])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

7

反応物 4

HCID 244Benzyl AlcoholHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2762196Boc-trans-4-(2-pyridinyl)-pyrrolidine-3-carboxylic acid

生成物 1

HCID 700235531-Tert-butyloxycarbonyl-trans-3-benzyloxycarbonylamino-4-(2-pyridyl)pyrrolidine

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 1-tert-butyloxycarbonyl-trans-4-(2-pyridyl)pyrrolidine-3-carboxylic acid from step 5 above (13 mmol) in toluene (50 mL) was added DIEA (3.0 mL, 17 mmol). The solution was cooled to 0° C. and diphenylphosphoryl azide (4.1 g, 15 mmol) was added. The resulting solution was stirred at 0° C. for 1 h and at ambient temperature for 4 h. Benzyl alcohol (2.8 g, 26 mmol) was added and the solution was refluxed for 3 h. The solution was cooled to ambient temperature, diluted with EtOAc, and washed with aqueous NaHCO3. The organic phase was separated, dried over MgSO4, filtered, and the solvents were removed in vacuo. The residue was purified by flash column chromatography using a gradient elution of 10-25% EtOAc:hexanes to give the title compound as an oil (3.9 g, TLC Rf=0.4, 1:3 EtOAc-hexanes; HPLC RT=6.67 min, method A).

後処理

  1. temperaturethe solution was refluxed for 3 h
  2. temperatureThe solution was cooled to ambient temperature
  3. washwashed with aqueous NaHCO3
  4. customThe organic phase was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed in vacuo
  8. customThe residue was purified by flash column chromatography
  9. washa gradient elution of 10-25% EtOAc

出典と根拠

ORDレコード
ord-e8b46c32a3784204809afd97ef45b796
出典データセット
uspto-grants-2003_08
特許番号
US06610692B1

反応ノート

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