(R)-Cyclohex-3-enecarboxylic acid → Benzyl (1R,3S,4R)-3,4-epoxycyclohexane-1-carboxylate

Reaction equation

[CH2:1]([O:8][C:9]([C@@H:11]1[CH2:16][CH2:15][CH:14]=[CH:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C@@H]1(C(O)=[O:24])CCC=CC1>>[CH2:1]([O:8][C:9]([C@@H:11]1[CH2:16][CH2:15][C@@H:14]2[C@@H:13]([O:24]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 736697(R)-Cyclohex-3-enecarboxylic acid

HCID 58822117(1R)-3-cyclohexene-1-carboxylic acid benzyl ester

Product 1

HCID 57432601Benzyl (1R*,3S*,4R)-3,4-epoxycyclohexane-1-carboxylate

Procedure

In a manner similar to that employed in Referential Example 99, (1R)-3-cyclohexene-1-carboxylic acid benzyl ester was prepared from (1R)-3-cyclohexene-1-carboxylic acid (J. Am. Chem. Soc, vol. 100, p. 5199 (1978)).

Sources & evidence

ORD record: ord-bd8a751f19264b2581cbd7596f7c4039
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576135B2

Reaction notes

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