Acetone → (3,4-Dihydroxycyclopentyl)methyl 4-nitrobenzoate

HRID 41156Notes

Reaction equation

HRID 41156 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([C:8]([O:10][CH2:11][CH:12]2CC=C[CH2:13]2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C[N+]1([O-])CC[O:23]CC1.C(O)CCC.S(=O)(O)[O-].[Na+].[CH3:37][C:38]([CH3:40])=[O:39]>[Os](=O)(=O)(=O)=O.O>[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([C:8]([O:10][CH2:11][CH:12]2[CH2:40][CH:38]([OH:39])[CH:37]([OH:23])[CH2:13]2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

8

Reactant 5

HCID 180AcetoneHCID 2631-ButanolHCID 82029Methyl morpholine oxideHCID 23665763Sodium BisulfiteHCID 67395687HCID 67395687, compound

Product 1

HCID 67399096(3,4-Dihydroxycyclopentyl)methyl 4-nitrobenzoate

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent

Procedure

Osmium tetroxide (235 μL, 0.75 mmol) was added to a solution of cyclopent-3-en-1-ylmethyl 4-nitrobenzoate (3.70 g, 15.0 mmol) and 4-methylmorpholine N-oxide (1.93 g, 16.5 mmol) in tent-butanol (6.7 mL)/water (40 mL)/acetone (13.3 mL). The solution was stirred at room temperature for 16 hours. Aqueous sodium bisulfite solution was added, and the solution was stirred for 30 min. The solution was then extracted with ethyl acetate, and the combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacua. The residue was purified by silica gel chromatography (Biotage 65i), eluting with 0-100% ethyl acetate/hexanes to give the title compound as a colorless oil. 1H NMR (500 MHz, CHCl3) δ 1.67-1.75 (m, 2H), 1.95-2.00 (m, 2H), 2.80-2.85 (m, 1H), 4.21 (quintet, J=4.1 Hz, 2H), 4.26 (d, J=6.7 Hz, 2H), 8.19 (d, J=8.7 Hz, 2H), 8.29 (d, J=8.7 Hz, 2H).

Workup

  1. stirringthe solution was stirred for 30 min
  2. extractionThe solution was then extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacua
  6. customThe residue was purified by silica gel chromatography (Biotage 65i)
  7. washeluting with 0-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-faf6072049554bb8af54694cf8324099
Source dataset
uspto-grants-2013_09
Patent number
US08530521B2

Reaction notes

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