6-Oxabicyclo[3.1.0]hexane → HCID 15372029, compound

HRID 1533490Notes

Reaction equation

HRID 1533490 reaction equation
N([Si:4]([CH3:7])([CH3:6])[CH3:5])=[N+]=[N-].[CH:8]12[O:13][CH:9]1[CH2:10][CH2:11][CH2:12]2.C([I:17])C=C>ClC1C=CC=CC=1>[I:17][C@H:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[O:13][Si:4]([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 92446-Oxabicyclo[3.1.0]hexaneHCID 11166Allyl iodideHCID 78378Azidotrimethylsilane

Product 1

HCID 15372029HCID 15372029, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a vial containing 0.03 grams of (S)-catalyst prepared as in Example 4 was added a solution of azidotrimethylsilane (0.17 g, 1.47 mmol), cyclopentene oxide (0.10 g, 1.19 mmol), and allyl iodide (0.41 g, 2.44 mmol) in chlorobenzene (3.0 mL). After 48 h the volatiles were removed at reduced pressure and the residue was purified by flash chromatography on 220-400 mesh silica with 98% hexane and 2% ether as eluant. The product (1S,2S)-1-iodo-2-trimethylsiloxycyclopentane (0.22 g, 75%) was isolated by distillation of the solvent. Anal. for C8H17OSiI. Calcd: C, 33.81; H, 6.03; 1, 44.65. Found: C, 34.60; H. 5.79; I, 44.21. 1 H NMR (CDCl3/TMS): δ 0.13 (s, 9 H), 1.53 (m, 1 H), 1.77 (m, 2 H), 1.97-2.12 (m, 2 H), 2.32 (m, 1 H), 4.01 (m, 1 H), 4.42 (m, 1 H). 13C NMR (CDCl3/TMS): δ 0.11, 22.37, 32.35, 34.64, 35.96, 82.48. [a]D25=+86.4°, c=1.04 g/100 mL chloroform. Chiral capillary gas chromatographic analysis at 110° C. on Cyclodex B stationary phase indicated that the enantiomeric excess of the product was 95%.

Workup

  1. additionTo a vial containing
  2. custom0.03 grams of (S)-catalyst prepared as in Example 4
  3. customAfter 48 h the volatiles were removed at reduced pressure
  4. customthe residue was purified by flash chromatography on 220-400 mesh silica with 98% hexane and 2% ether as eluant

Sources & evidence

ORD record
ord-d13714c3b75b49d38c7e79119e4656cf
Source dataset
uspto-grants-2001_03
Patent number
US06207847B1

Reaction notes

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