Allyl bromide → HCID 12624052, compound

HRID 1533489Notes

Reaction equation

HRID 1533489 reaction equation
N([Si:4]([CH3:7])([CH3:6])[CH3:5])=[N+]=[N-].[CH:8]12[O:14][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13]2.C([Br:18])C=C>ClC1C=CC=CC=1>[Br:18][C@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@@H:9]1[O:14][Si:4]([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 9246Cyclohexene oxideHCID 78378Azidotrimethylsilane

Product 1

HCID 12624052HCID 12624052, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a vial containing 0.03 grams of this (S)-catalyst was added a solution of azidotrimethylsilane (0.34 g, 2.95 mmol) and cyclohexene oxide (0.24 g, 2.45 mmol) in a mixture of allyl bromide (4.0 mL) and chlorobenzene (4.0 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-bromo-2-trimethysiloxycyclohexane (0.44 g, 71%) was isolated by distillation of the solvent at reduced pressure. Anal. for C9H19OSiBr: Calcd: C, 43.03; H, 7.62; Br, 31.80; found: C, 43.06; H, 7.69; Br, 31.78. 1H NMR: d 0.19 (s, 9 H), 1.24-1.46 (m, 3 H), 1.64-1.87 (m, 3 H), 2.01 (m, 1 H), 2.35 (m, 1 H), 3.66 (m, 1 H), 3.87 (m, 1 H). 13C NMR: d 24.15, 25.70, 34.96, 35.62, 58.44, 75.38. [a]D25=+39.0, c=1.02 g/100 mL chloroform. Chiral capillary gas chromatographic analysis at 120° C. on Cyclodex B stationary phase indicated that the enantiomeric excess of the product was 85%.

Workup

  1. additionTo a vial containing 0.03 grams of this (S)-catalyst
  2. customAfter 48 h the volatiles were removed at reduced pressure
  3. 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-52150a14696e400585963cf661c837bf
Source dataset
uspto-grants-2001_03
Patent number
US06207847B1

Reaction notes

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