Triethylamine → tert-Butyl 1-((benzo[b]thiophen-5-yloxy)methyl)pyrrolidine-2-carboxylate

HRID 2267322ノート

反応式

HRID 2267322 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[S:34]1[CH:38]=[CH:37][C:36]2[CH:39]=[C:40]([OH:43])[CH:41]=[CH:42][C:35]1=2.[C:44]([O:48][C:49](N1CCC[C@H]1CO)=[O:50])([CH3:47])([CH3:46])[CH3:45].[CH2:58]([N:60]([CH2:63][CH3:64])[CH2:61][CH3:62])C>ClCCl>[S:34]1[CH:38]=[CH:37][C:36]2[CH:39]=[C:40]([O:43][CH2:58][N:60]3[CH2:63][CH2:64][CH2:62][CH:61]3[C:49]([O:48][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:50])[CH:41]=[CH:42][C:35]1=2

参加物

7

反応物 5

HCID 8471TriethylamineHCID 11776Triphenylphosphine2 回HCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643448(S)-(-)-N-Boc-prolinolHCID 12203499Benzo[b]thiophen-5-ol

生成物 1

HCID 60204374tert-Butyl 1-((benzo[b]thiophen-5-yloxy)methyl)pyrrolidine-2-carboxylate収率 103.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

Polymer supported triphenyl phosphine (5.12 g, 13.32 mmol, 2.6 mmol/g loading) was suspended in dichloromethane (15 mL) cooled to 0° C. in an ice/water bath. Diisopropyl azodicarboxylate (2.69 g, 13.3 mmol, 2.6 mL) was added dropwise and the mixture was stirred for 10 min. A solution of benzo[b]thiophen-5-ol (1.20 g, 7.99 mmol) and (S)-tert-butyl-2-(hydroxymethyl)pyrrolidine-1-carboxylate (1.34 g, 6.66 mmol) dissolved in dichloromethane (20 mL) was added dropwise at 0° C. The cooling bath was removed, triethylamine (1.35 g, 13.3 mmol) was added, and the mixture was stirred for 16 h. The polymer bound triphenylphosphine was removed by filtration and washed with dichloromethane (3×10 mL). The organic layer was separated, dried over sodium sulfate (200 mg), filtered through a coarse frit (to remove the sodium sulfate), and condensed in vacuo to give a white solid (2.3 g). The crude product was purified by flash chromatography (EtOAc/hexane 1:1) to yield the title compound as a white solid (1.95 g, 55%). MS (M+H)+ 334.

後処理

  1. additionwas added dropwise at 0° C
  2. customThe cooling bath was removed
  3. stirringthe mixture was stirred for 16 h
  4. customwas removed by filtration
  5. washwashed with dichloromethane (3×10 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate (200 mg)
  8. filtrationfiltered through a coarse frit (
  9. customto remove the sodium sulfate), and
  10. customcondensed in vacuo

出典と根拠

ORDレコード
ord-5f14406bc8ec49d19b6badb6c5990ddb
出典データセット
uspto-grants-2010_12
特許番号
US07858785B2

反応ノート

読み込み中…