m-Chloroperbenzoic acid → (1R,2R,3S,5S)-3-(Hydroxymethyl)-6-oxabicyclo[3.1.0]hexan-2-ol

HRID 552722Notes

Reaction equation

HRID 552722 reaction equation
[OH:1][CH2:2][C@H:3]1[C@@H:7]([OH:8])[CH:6]=[CH:5][CH2:4]1.ClC1C=CC=C(C(OO)=[O:17])C=1>C(Cl)Cl>[OH:1][CH2:2][C@@H:3]1[CH2:4][C@H:5]2[C@H:6]([O:17]2)[C@@H:7]1[OH:8]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10887865(1S,5S)-5-(hydroxymethyl)cyclopent-2-enol

Product 1

HCID 58944591(1R,2R,3S,5S)-3-(Hydroxymethyl)-6-oxabicyclo[3.1.0]hexan-2-olYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1S,5S)-5-(hydroxymethyl)cyclopent-2-en-1-ol (3.19 g, 27.9 mmol) (An, G.-I.; Rhee, H. Nucleosides Nucleotides 2002, 21, 65-72) in DCM (143 mL) at 0° C. was added 3-chloroperbenzoic acid (7.52 g, 33.5 mmol) and the mixture was stirred at room temperature for 4 hours. Silica gel (20 g) was added, the mixture was concentrated to dryness and was purified via flash chromatography (0 to 100% EtOAc/DCM) to afford the title compound (2.75 g, 76%).

Workup

  1. additionSilica gel (20 g) was added
  2. concentrationthe mixture was concentrated to dryness
  3. customwas purified via flash chromatography (0 to 100% EtOAc/DCM)

Sources & evidence

ORD record
ord-de43719be1a84f47b32fbbc5ead237e6
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

Loading…