Vinyl Acetate → HCID 86600247, compound

HRID 1243804Notes

Reaction equation

HRID 1243804 reaction equation
[N:1]([CH2:4][CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:8]=1)[OH:6])=[N+:2]=[N-:3].[C:14](OC=C)(=[O:16])[CH3:15]>C1(C)C=CC=CC=1>[N:1]([CH2:4][C@@H:5]([O:6][C:14](=[O:16])[CH3:15])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[N:8]=1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 21928039HCID 21928039, compound

Product 1

HCID 86600247HCID 86600247, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Dissolved 2-Azido-1-(6-methyl-pyridin-2-yl)-ethanol (4.300 g, 24.130 mmol) into 200 mL of toluene. To this was added vinyl acetate (9.22 mL, 100.00 mmol) and Lipase PS-C II (4.00 g). The mixture stirred for 4.5 h at RT and was monitored by 1H NMR. The reaction mixture was filtered through a bed of celite and rinsed with 100 mL of toluene. The filtrate was concentrated in vacuo. Dissolved residue into CH2Cl2, applied to a SiO2 Column and purified (5–30% EtOAc/hexanes) to give 2.20g of acetic acid (R)-2-azido-1-(6-methyl-pyridin-2-yl)-ethyl ester and 2.11 of (S)-2-azido-1-(6-methyl-pyridin-2-yl)-ethanol, ee % >99.

Workup

  1. filtrationThe reaction mixture was filtered through a bed of celite and
  2. washrinsed with 100 mL of toluene
  3. concentrationThe filtrate was concentrated in vacuo
  4. custompurified (5–30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-9f5aea0670a9427daaafc1eb68709b03
Source dataset
uspto-grants-2006_10
Patent number
US07119102B2

Reaction notes

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