Triethylamine → (5R)-5,6-bis(nitrooxy)hexyl 1-chloroethyl carbonate

HRID 1361904Notes

Reaction equation

HRID 1361904 reaction equation
Cl[C:2]([O:4][CH:5]([Cl:7])[CH3:6])=[O:3].[N+:8]([O-:22])([O:10][CH2:11][C@H:12]([O:18][N+:19]([O-:21])=[O:20])[CH2:13][CH2:14][CH2:15][CH2:16][OH:17])=[O:9].C(N(CC)CC)C>C(Cl)Cl>[C:2](=[O:3])([O:4][CH:5]([Cl:7])[CH3:6])[O:17][CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]([O:18][N+:19]([O-:21])=[O:20])[CH2:11][O:10][N+:8]([O-:22])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5213051-Chloroethyl chloroformateHCID 59556786(2R)-6-hydroxyhexane-1,2-diyl dinitrate

Product 1

HCID 59370672(5R)-5,6-bis(nitrooxy)hexyl 1-chloroethyl carbonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Chloroethyl chloroformate (6.42 mL, 58.9 mmol) was added dropwise to a stirred solution of (2R)-6-hydroxyhexane-1,2-diyl dinitrate (12 g, 53.5 mmol) and triethylamine (8.95 mL, 64.2 mmol) in DCM (268 mL) at 0° C. After 2 h, the solution was washed with water, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 5-40% EtOAc/hexanes to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3) δ 6.40 (q, J=6.0 Hz, 1H), 5.28 (ddd, J=13.0, 6.2, 3.0 Hz, 1H), 4.74 (dd, J=13.0, 3.0 Hz, 1H), 4.47 (dd, J=13.0, 6.5 Hz, 1H), 4.25-4.16 (m, 2H), 1.82 (d, J=6.0 Hz, 3H), 1.82-1.71 (m, 4H), 1.63-1.46 (m, 2H).

Workup

  1. washthe solution was washed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with 5-40% EtOAc/hexanes

Sources & evidence

ORD record
ord-32a73ad621074bada1a5750b9600c100
Source dataset
uspto-grants-2011_02
Patent number
US07880014B2

Reaction notes

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