Sodium borohydride → Npc182939

HRID 414273

반응식

HRID 414273 반응식
[CH3:1][C@H:2]1[C@@H:12]2[CH2:13][CH2:14][C@:15]3([CH3:19])[O:17][O:18][C@:11]42[C@H:5]([C@@H:6]([CH3:20])[C:7]([O:9][C@@H:10]4[O:16]3)=[O:8])[CH2:4][CH2:3]1.[BH4-].[Na+].CC(O)=O.CO>CO>[CH3:1][C@H:2]1[C@@H:12]2[CH2:13][CH2:14][C:15]3([CH3:19])[O:17][O:18][C@:11]42[C@H:5]([C@@H:6]([CH3:20])[C@@H:7]([OH:8])[O:9][C@@H:10]4[O:16]3)[CH2:4][CH2:3]1

참가 물질

5

반응물 3

HCID 4311764Sodium borohydride2회HCID 9838675Qing Hau Sau2회HCID 10129899Acetic acid methanol

생성물 1

HCID 456410Npc182939수율 75%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Artemisinin (compound 3) (0.5 g, 1.8 mmole) in 40 mL of MeOH was cooled in an ice-bath to 0°-5° C. To the solution was added in small portions 0.25 g (6.6 mmole) of NaBH4 over a period of 30 minutes. The solution was stirred at 0°-5° C. for 2 hours after the addition of NaBH4 was complete. The solution was neutralized with 30% AcOH/MeOH and evaporated to dryness under reduced pressure. The white residue was extracted 3 times with 50 mL of EtOAc. The EtOAc extracts were combined, filtered, and evaporated to dryness to give 0.38 g (75%) of white needles mp 152°-154° C. (dec). Recrystallization from EtOAc-hexane raised the melting point to 153°-155° C. (lit. mp 153°-154° C.).

후처리

  1. customevaporated to dryness under reduced pressure
  2. extractionThe white residue was extracted 3 times with 50 mL of EtOAc
  3. filtrationfiltered
  4. customevaporated to dryness

출처 및 근거

ORD 기록
ord-42dfb6d64921409b843d06906f4bf799
출처 데이터셋
uspto-grants-1988_12
특허 번호
US04791135

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