Tetrahydrofuran → tert-Butyl (5S,7S)-1-oxo-2-oxaspiro[4.4]non-8-en-7-ylcarbamate

HRID 1747143노트

반응식

HRID 1747143 반응식
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C@@:12]([CH2:18][CH2:19][O:20][Si](C(C)(C)C)(C)C)([C:14]([O:16]C)=O)[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CCOC(C)=O>[O:16]=[C:14]1[C@:12]2([CH:11]=[CH:10][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13]2)[CH2:18][CH2:19][O:20]1

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 86708127(1S,4S)-methyl 4-(tert-butoxycarbonylamino)-1-(2-(tert-butyldimethylsilyloxy)ethyl)cyclopent-2-enecarboxylate

생성물 1

HCID 86708140tert-Butyl (5S,7S)-1-oxo-2-oxaspiro[4.4]non-8-en-7-ylcarbamate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a solution of the product of Step D (1149 g, 2.875 mol) and THF (5.75 L) was added TBAF (1M in THF, 2.875 L) over ˜1 h. The reaction was stirred for 1 h at rt, and diluted with EtOAc. The organic layer was washed with brine, diluted with heptanes and the organic layer was further washed with water and brine. The organic layer was evaporated, the crystallized product was filtered, and washed with heptanes to provide the product of Step E as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) d=5.86-5.98 (m, 3H), 5.67 (d, J=5.4 Hz, 3H), 5.03-5.20 (m, 2H), 4.76-4.87 (m, 3H), 4.28 (t, J=7.0 Hz, 5H), 2.08-2.31 (m, 8H), 1.99 (d, J=2.4 Hz, 3H), 1.34 (s, 25H).

후처리

  1. washThe organic layer was washed with brine
  2. additiondiluted with heptanes
  3. washthe organic layer was further washed with water and brine
  4. customThe organic layer was evaporated
  5. filtrationthe crystallized product was filtered
  6. washwashed with heptanes

출처 및 근거

ORD 기록
ord-e92d891a87b94cb4ae110db654fa821b
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150532B2

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