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Lithium borohydride → tert-Butyl N-[(1R,2S)-rel-2-(4-hydroxyphenyl)cyclopropyl]carbamate

HRID 1844243
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인쇄 미리보기

반응식

HRID 1844243 반응식
[Li+].[BH4-].C([O:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[CH2:15][C@H:14]2[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:9][CH:8]=1)C=C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[CH2:15][C@H:14]2[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[CH:9][CH:8]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 4148881Lithium borohydrideHCID 86672577Tert-butyl(trans)-2-[4-(allyloxy)phenyl]cyclopropylcarbamate2회

생성물 1

HCID 86672576tert-Butyl N-[(1R,2S)-rel-2-(4-hydroxyphenyl)cyclopropyl]carbamate수율 90%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028
Tetrahydrofuran
용매

실험 절차

LiBH4 (0.34 g, 15.54 mmol) was added to a solution of Pd(PPh3)4 (0.15 g, 0.13 mmol) and tert-butyl(trans)-2-[4-(allyloxy)phenyl]cyclopropylcarbamate (Intermediate I, 0.75 g, 2.59 mmol) in dry THF (20 mL) and stirred at room temperature for 1 h. After removal of the solvent, the residue was dissolved in EtOAc (25 mL), acidified with HCl (10% aqueous solution, 2 mL), and washed with water (25 mL) and brine (25 mL). The organic layer was dried over anhydrous Na2SO4 and filtered. After removal of the solvent, the residue was purified by column chromatography on silica gel (10%-20% EtOAc/Hexanes), affording 0.58 g of tert-butyl(trans)-2-(4-hydroxyphenyl)cyclopropylcarbamate [Rf=0.3 (30% EtOAc/Hexanes), pale yellow foam, 90% yield].

후처리

  1. customAfter removal of the solvent
  2. dissolutionthe residue was dissolved in EtOAc (25 mL)
  3. washwashed with water (25 mL) and brine (25 mL)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customAfter removal of the solvent
  7. customthe residue was purified by column chromatography on silica gel (10%-20% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-7efc1b8a183d4426bc66494227fa2af6
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08946296B2

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