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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
ノート
印刷プレビュー

反応式

HRID 511490 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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]carbamate2 回

生成物 1

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

試薬・触媒・溶媒 2

HCID 6386tert-Butanol
溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-4f73c6ef9a0f456f98792c19e0b6cf13
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09096624B2

反応ノート

読み込み中…

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