Water → HCID 86682289, compound

HRID 540464Notes

Reaction equation

HRID 540464 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2CC=C[CH2:9]2)[CH:5]=CC=1OC.C[N+]1([O-])[CH2:21][CH2:20][O:19][CH2:18]C1.[C:23]([OH:27])([CH3:26])(C)[CH3:24].[OH2:28]>[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:9][CH:24]([OH:28])[CH:23]([OH:27])[CH2:26]2)[CH:5]=[CH:21][C:20]=1[O:19][CH3:18]

Participants

6

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 86682288HCID 86682288, compound

Product 1

HCID 86682289HCID 86682289, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a 100 mL RBF were added 2-bromo-4-(cyclopent-3-en-1-yl)-1-methoxybenzene (1.9 g, 7.51 mmol), NMO (2.64 g, 22.5 mmol), osmium tetroxide (0.942 mL, 0.075 mmol, 2.5% in t-BuOH), t-butanol (13 mL) and water (13 mL). The resulting reaction mixture was stirred at rt over the weekend. Volatiles were removed. Crude material was dissolved in 100 mL EtOAc and washed with 50 mL water. Organics were dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel column chromatography, eluting with 80% EtOAc in hexane to give 4-(3-bromo-4-methoxyphenyl)cyclopentane-1,2-diol (1.7 g) as white solid. 1H NMR (500 MHz, CDCl3): δ 7.39 (s, 1H), 7.10 (d, 1H), 6.85 (d, 1H), 4.37 (m, 2H), 3.91 (s, 3H), 3.55 (m, 1H), 2.46 (b, 2H), 2.18 (m, 2H), 1.88 (m, 2H).

Workup

  1. customThe resulting reaction mixture
  2. customVolatiles were removed
  3. dissolutionCrude material was dissolved in 100 mL EtOAc
  4. washwashed with 50 mL water
  5. dry with materialOrganics were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography
  9. washeluting with 80% EtOAc in hexane

Sources & evidence

ORD record
ord-37bb2c0e91374447a56d5b18edc644de
Source dataset
uspto-grants-2014_10
Patent number
US08871738B2

Reaction notes

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