Sodium borohydride → tert-Butyl ((2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-yl)carbamate

HRID 218414노트

반응식

HRID 218414 반응식
[CH2:1]([C@H:4]1[C:8](=[O:9])[N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:6]([C:17](OCC)=[O:18])[CH2:5]1)[CH:2]=[CH2:3].[BH4-].[Na+]>CO.O>[OH:18][CH2:17][C@@H:6]([NH:7][C:10](=[O:11])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:5][C@H:4]([CH2:8][OH:9])[CH2:1][CH:2]=[CH2:3]

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 5287387(2S,4R)-1-tert-butyl 2-ethyl 4-allyl-5-oxopyrrolidine-1,2-dicarboxylate

생성물 1

HCID 58011569tert-Butyl ((2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-yl)carbamate수율 85%

시약·촉매·용매 1

HCID 22242641Methanol--water (1/1)용매

실험 절차

To a solution of (2S,4R)-1-tert-butyl 2-ethyl 4-allyl-5-oxopyrrolidine-1,2-dicarboxylate (30 g, 0.1 mol) in MeOH/H2O (700/70 mL) was added NaBH4 (25 g, 0.66 mol), the result mixture was stirred 1 hr at rt and quenched with sat. aq. NH4Cl (300 mL). The organic solvent was removed under vacuum and extracted with EtOAc (3×250 mL). The combined organic phases were washed with brine (250 mL) and dried over anhydrous Na2SO4, filtered and evaporated to afford crude tert-butyl (2S,4R)-1-hydroxy-4-(hydroxymethyl)hept-6-en-2-ylcarbamate (22 g, 85%). It was used in the next step without further purification.

후처리

  1. customquenched with sat. aq. NH4Cl (300 mL)
  2. customThe organic solvent was removed under vacuum
  3. extractionextracted with EtOAc (3×250 mL)
  4. washThe combined organic phases were washed with brine (250 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-b212dd756c504b4da9b6c14038dd85ab
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198453B2

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