Pyridine → methyl(4R)-3-(6-cyanohexyl)-2-oxo-1,3-oxazolidine-4-carboxylate

HRID 2215078

Reaction equation

HRID 2215078 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C@@H:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:11][OH:12])#[N:2].N1C=CC=CC=1.[C:23](Cl)(Cl)=[O:24]>ClCCl.C1(C)C=CC=CC=1>[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C@@H:10]([C:13]([O:15][CH3:16])=[O:14])[CH2:11][O:12][C:23]1=[O:24])#[N:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6371PhosgeneHCID 86606385methyl N-(6-cyanohexyl)-D-serinate

Product 1

HCID 69659745methyl(4R)-3-(6-cyanohexyl)-2-oxo-1,3-oxazolidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of amine 2-1 (620 mg) and pyridine (0.48 mL) in dichloromethane (10 mL) at 0° C. was added a solution of phosgene in toluene (1.72 mL, 1.9 M) and the mixture was stirred at the temperature for 1 h. The mixture was diluted with dichloromethane and washed with 1 N HCl and brine, and dried over Na2SO4. Filtration and concentration of the filtrate gave the crude product which was purified by chromatography. Eluting with 60% ethyl acetate in hexanes afforded the desired product 2-2 (560 mg). 1H NMR (400 MHz, acetone-d6): δ 4.61 (dd, 1H), 4.52 (t, 1H), 4.35 (dd, 1H), 3.80 (s, 3H), 3.48 (m, 1H), 3.15 (m, 1H), 2.47 (t, 2H), 1.75–1.35 (m, 8H).

Workup

  1. washwashed with 1 N HCl and brine
  2. dry with materialdried over Na2SO4
  3. filtrationFiltration and concentration of the filtrate
  4. customgave the crude product which
  5. customwas purified by chromatography
  6. washEluting with 60% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-82ec6ef3a7c1491798f57d621906b4a4
Source dataset
uspto-grants-2006_09
Patent number
US07109223B2

Linked notes

Loading…