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

HRID 41152Notes

Reaction equation

HRID 41152 reaction equation
[CH3:1][O:2][C@@H:3]1[C@@H:7]([O:8][N+:9]([O-:11])=[O:10])[CH2:6][C@H:5]([C:12]([O:14]C)=[O:13])[CH2:4]1.COC1C(O[N+]([O-])=O)CC(C(OC)=O)C1>>[CH3:1][O:2][CH:3]1[CH:7]([O:8][N+:9]([O-:11])=[O:10])[CH2:6][CH:5]([C:12]([OH:14])=[O:13])[CH2:4]1

Participants

3

Reactant 2

HCID 66753156methyl (1R,3S,4S)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylateHCID 67396922methyl (1RS,3RS,4RS)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylate

Product 1

HCID 46220317(1RS,3RS,4SR)-3-methoxy-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,3SR,4RS)-3-methoxy-4-(nitrooxy)cyclopentanecarboxylate. 1H NMR (500 MHz, CDCl3) δ 2.17-2.30 (m, 2H), 2.32-2.43 (m, 2H), 2.90 (m, 1H), 3.39 (s, 3H), 3.89 (m, 1H), 5.30 (dd, J=6.1, 10.6 Hz, 1H).

Sources & evidence

ORD record
ord-ddb9dcee8e9a4299b9d7a9081610ec02
Source dataset
uspto-grants-2013_09
Patent number
US08530521B2

Reaction notes

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