Water → tert-butyl (3aR,5S,6S,6aS)-6-bromo-3a-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-5-ylcarbamate

HRID 1747145노트

반응식

HRID 1747145 반응식
[OH:1][CH2:2][CH2:3][C@@:4]1([CH2:17][OH:18])[CH2:8][C@H:7]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[CH:5]1.[Br:19]N1C(=O)CCC1=O.O>CCOC(C)=O>[Br:19][C@@H:6]1[C@H:5]2[O:1][CH2:2][CH2:3][C@@:4]2([CH2:17][OH:18])[CH2:8][C@@H:7]1[NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:13])[CH3:14]

참가 물질

5

반응물 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 86708141tert-butyl ((1S,4S)-4-(2-hydroxyethyl)-4-(hydroxymethyl)cyclopent-2-en-1-yl)carbamate

생성물 1

HCID 86708147tert-butyl (3aR,5S,6S,6aS)-6-bromo-3a-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-5-ylcarbamate

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a chilled solution of the product of Step F (343.60 g) in EtOAc (4 L) was added N-bromosuccinimide (237.60 g) followed by stirring at rt for 18 h. To the mixture was added water (5 mL) and the reaction heated to 60° C. for 30 min. The reaction was filtered, the filtrate was washed with aqueous sodium thiosulfate until the organic layer was negative for peroxides. The organic layer was washed with aqueous Na2CO3 (10%), dried (Na2SO4) and the reaction was concentrated under reduced pressure. Near the end of the concentration, heptane (1.2 L) was added, and the product was collected by filtration to provide the product of Step G. 1H NMR (400 MHz, CHLOROFORM-d) δ=4.78-4.91 (m, 1H), 4.41 (br. s., 1H), 4.31 (s, 2H), 3.88-3.98 (m, 1H), 3.61-3.77 (m, 3H), 2.08-2.24 (m, 1H), 1.82 (m, 2H), 1.60-1.70 (t, 1H), 1.45 (s, 9H)

후처리

  1. temperaturethe reaction heated to 60° C. for 30 min
  2. filtrationThe reaction was filtered
  3. washthe filtrate was washed with aqueous sodium thiosulfate until the organic layer
  4. washThe organic layer was washed with aqueous Na2CO3 (10%)
  5. dry with materialdried (Na2SO4)
  6. concentrationthe reaction was concentrated under reduced pressure
  7. concentrationNear the end of the concentration, heptane (1.2 L)
  8. additionwas added
  9. filtrationthe product was collected by filtration

출처 및 근거

ORD 기록
ord-5be5f0849f0141229085f3cc938711b9
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150532B2

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