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tert-Butanol → (3R,4R)-1-Benzyloxycarbonyl-3-(1-tert-butoxycarbonylaminocyclopropyl)-4-methylpyrrolidine

HRID 1954589
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HRID 1954589 반응식
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([CH3:16])[C@@H:13]([C:17]2(C(O)=O)[CH2:19][CH2:18]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.C([N:42]([CH2:45]C)CC)C.[C:47]([OH:51])([CH3:50])([CH3:49])[CH3:48]>>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([CH3:16])[C@@H:13]([C:17]2([NH:42][C:45]([O:51][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:30])[CH2:18][CH2:19]2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 695653671-[(3S,4R)-1-Benzyloxycarbonyl-4-methyl-3-Pyrrolidinyl]cyclopropanecarboxylic acid

생성물 1

HCID 54433189(3R,4R)-1-Benzyloxycarbonyl-3-(1-tert-butoxycarbonylaminocyclopropyl)-4-methylpyrrolidine수율 58%

실험 절차

1-[(3S,4R)-1-Benzyloxycarbonyl-4-methyl-3-pyrrolidinyl]cyclopropanecarboxylic acid (1.20 g, 3.66 mmol) was dissolved in tert-butyl alcohol (50 ml), and the solution was mixed with diphenylphosphoryl azide (0.946 ml, 4.39 mmol) and triethylamine (1.02 ml, 7.32 mmol) and heated under reflux for 19 hours. After completing the reaction, the solvent was evaporated and the resulting residue was purified by silica gel column chromatography (silica gel, 120 ml; ethyl acetate:hexane=1:2), to thereby obtain 0.793 g (58%) of the title compound.

후처리

  1. temperatureheated
  2. temperatureunder reflux for 19 hours
  3. customthe reaction
  4. customthe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography (silica gel, 120 ml; ethyl acetate:hexane=1:2)

출처 및 근거

ORD 기록
ord-977259c0989a43fa96e94a539044a151
출처 데이터셋
uspto-grants-2000_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06121285

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