(5R)-5,6-bis(nitrooxy)hexyl 4-nitrobenzoate → (2R)-5-hydroxypentane-1,2-diyl dinitrate

HRID 1361914Notes

Reaction equation

HRID 1361914 reaction equation
[N+](C1C=CC(C(OCCCC[C@@H](O[N+]([O-])=O)CO[N+]([O-])=O)=O)=CC=1)([O-])=O.[N+](C1C=CC(C([O:36][CH2:37][CH2:38][CH2:39][C@@H:40]([O:46][N+:47]([O-:49])=[O:48])[CH2:41][O:42][N+:43]([O-:45])=[O:44])=O)=CC=1)([O-])=O>>[N+:43]([O-:45])([O:42][CH2:41][C@H:40]([O:46][N+:47]([O-:49])=[O:48])[CH2:39][CH2:38][CH2:37][OH:36])=[O:44]

Participants

3

Reactant 2

HCID 57456806(5R)-5,6-bis(nitrooxy)hexyl 4-nitrobenzoateHCID 86622533(4R)-4,5-bis(nitrooxy)pentyl 4-nitrobenzoate

Product 1

HCID 59370678(2R)-5-hydroxypentane-1,2-diyl dinitrate

Procedure

The title compound was prepared by following the procedure for example 6 in WO2005070868(A 1), except that the reagent (5R)-5,6-bis(nitrooxy)hexyl 4-nitrobenzoate was replaced by (4R)-4,5-bis(nitrooxy)pentyl 4-nitrobenzoate. 1H NMR (500 MHz, CD3CN) δ 5.42 (dq, J=2.6, 6.6 Hz, 1H), 4.84 (dd, J=2.6, 12.9 Hz, 1H), 4.48 (dd, J=6.2, 13.0 Hz, 1H), 3.54 (t, J=6.3 Hz, 2H), 1.82 (q, J=7.4 Hz, 2H), 1.54-1.68 (m, 2H).

Sources & evidence

ORD record
ord-ed18330db532482bb689acbbb1833c2b
Source dataset
uspto-grants-2011_02
Patent number
US07880014B2

Reaction notes

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