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Water → tert-butyl[7-(3,4-dihydroxycyclopentyl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]carbamate

HRID 511490
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HRID 511490 반응식
[CH:1]1([C:6]2[CH:7]=[CH:8][C:9]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[C:10]3[C:14]=2[CH2:13][N:12]([CH3:15])[C:11]3=[O:16])[CH2:5][CH:4]=[CH:3][CH2:2]1.C[N+]1([O-])CC[O:29]CC1.[OH2:33]>CC(O)(C)C.CCOC(C)=O>[OH:33][CH:4]1[CH:3]([OH:29])[CH2:2][CH:1]([C:6]2[CH:7]=[CH:8][C:9]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[C:10]3[C:14]=2[CH2:13][N:12]([CH3:15])[C:11]3=[O:16])[CH2:5]1
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참가 물질

6

반응물 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 86695308tert-butyl [7-(cyclopent-3-en-1-yl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]carbamate2회

생성물 1

HCID 86695307tert-butyl[7-(3,4-dihydroxycyclopentyl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]carbamate수율 99%

시약·촉매·용매 2

HCID 6386tert-Butanol
용매
HCID 8857Ethyl Acetate용매

실험 절차

To a solution of tert-butyl [7-(cyclopent-3-en-1-yl)-2-methyl-3-oxo-2,3-dihydro-1H-isoindol-4-yl]carbamate (Compound 243C: 33 mg, 0.10 mmol) in t-BuOH (1 mL) and H2O (1 mL) were added N-methylmorpholine N-oxide (14 mg, 0.12 mmol) and potassium osmate dihydrate (0.37 mg, 0.0010 mmol). The resulting mixture was stirred at rt overnight. The mixture was diluted with EtOAc (30 mL), washed with brine (10 mL), and dried over anhydrous sodium sulfate. The solvents were evaporated under reduced pressure to give the title compound as a white solid, 36 mg, 99% yield. 1H NMR (CDCl3): 1.52 (s, 9H), 1.90-1.94 (m, 2H), 2.14-2.19 (m, 2H), 2.34 (br s, 2H), 3.17 (s, 3H), 3.56 (m, 1H), 4.33 (s, 2H), 4.39 (m, 2H), 7.26 (d, J=8.6 Hz, 1H), 8.14 (d, J=8.6 Hz, 1H), 9.50 (br s, 1H). MS (ES+): m/z=363.16 [MH+]. HPLC: tR=3.44 min (ZQ3, polar—5 min).

후처리

  1. washwashed with brine (10 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvents were evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-4f73c6ef9a0f456f98792c19e0b6cf13
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09096624B2

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