Isoidide mononitrate → (3R,3aR,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl 4-nitrophenyl carbonate

HRID 1643412Notes

Reaction equation

HRID 1643412 reaction equation
Cl.[N+:2]([O-])([O:4]C1CCNCC1)=[O:3].O[C@H:13]1[C@H:17]2O[CH2:19][C@@H:20]([O:21][C:22](=[O:36])CCC[C@H](O[N+]([O-])=O)CO[N+]([O-])=O)[C@H:16]2O[CH2:14]1.[N+:37]([O-:49])([O:39][C@@H:40]1[CH2:44][O:43][C@@H:42]2[C@H:45]([OH:48])[CH2:46][O:47][C@H:41]12)=[O:38]>>[C:22](=[O:36])([O:21][C:20]1[CH:19]=[CH:14][C:13]([N+:2]([O-:4])=[O:3])=[CH:17][CH:16]=1)[O:48][C@@H:45]1[CH2:46][O:47][C@@H:41]2[C@H:40]([O:39][N+:37]([O-:49])=[O:38])[CH2:44][O:43][C@H:42]12

Participants

4

Reactant 3

HCID 182267Isoidide mononitrateHCID 58209439(S)-((3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl) 5,6-bis(nitrooxy)hexanoateHCID 66753481Piperidin-4-yl nitrate hydrochloride

Product 1

HCID 59178160(3R,3aR,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl 4-nitrophenyl carbonate

Procedure

The title compound was prepared by following the procedure for INTERMEDIATE 13 Step H, except that the reagent (S)-((3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl)5,6bis(nitrooxy)hexanoate was replaced by (3R,3aS,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl nitrate. 1H-NMR (300 MHz, CDCl3); δ 8.37-8.21 (2H, m), 7.46-7.33 (2H, m), 5.41-5.29 (1H, m), 5.20-5.05 (1H, m), 4.97-4.75 (2H, m), 4.25-3.91 (4H, m).

Sources & evidence

ORD record
ord-7af6ea8badbe423daa3d951e8e81a18c
Source dataset
uspto-grants-2012_02
Patent number
US08119806B2

Reaction notes

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