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

HRID 511490Notes

Reaction equation

HRID 511490 reaction equation
[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

Participants

6

Reactant 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×

Product 1

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

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-4f73c6ef9a0f456f98792c19e0b6cf13
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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