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

HRID 2267322노트

반응식

HRID 2267322 반응식
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

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 11776Triphenylphosphine2회HCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 643448(S)-(-)-N-Boc-prolinolHCID 12203499Benzo[b]thiophen-5-ol

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5f14406bc8ec49d19b6badb6c5990ddb
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07858785B2

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