methyl (1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylate → (1RS,3RS,4RS)-3-fluoro-4-(nitrooxy)cyclopentanecarboxylic acid

HRID 41154Notes

Reaction equation

HRID 41154 reaction equation
CO[C@@H]1[C@@H](O[N+]([O-])=O)C[C@H](C(OC)=O)C1.[F:16][CH:17]1[CH:21]([O:22][N+:23]([O-:25])=[O:24])[CH2:20][CH:19]([C:26]([O:28]C)=[O:27])[CH2:18]1>>[F:16][CH:17]1[CH:21]([O:22][N+:23]([O-:25])=[O:24])[CH2:20][CH:19]([C:26]([OH:28])=[O:27])[CH2:18]1

Participants

3

Reactant 2

HCID 66753156methyl (1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylateHCID 67396836methyl (1RS,3RS,4RS)-3-fluoro-4-(nitrooxy)cyclopentanecarboxylate

Product 1

HCID 67395802(1RS,3RS,4RS)-3-fluoro-4-(nitrooxy)cyclopentanecarboxylic acid

Procedure

The title compound was prepared by following step D for example 1, except that the reagent (+)-methyl (1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylate was replaced by methyl (1RS,3RS,4RS)-3-fluoro-4-(nitrooxy)cyclopentanecarboxylate. 1H NMR (500 MHz, CDCl3) δ 2.13-2.52 (m, 1H), 2.30-2.52 (m, 2H), 2.61-2.69 (m, 1H), 3.16 (m, 1H), 5.10 (m, 1H), 5.47 (m, 1H).

Sources & evidence

ORD record
ord-e1cbedd68204400092302f1eb5fd0743
Source dataset
uspto-grants-2013_09
Patent number
US08530521B2

Reaction notes

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