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

HRID 1361904ノート

反応式

HRID 1361904 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-32a73ad621074bada1a5750b9600c100
出典データセット
uspto-grants-2011_02
特許番号
US07880014B2

反応ノート

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