Chloroiodomethane → (1S,2R,4S,5R)-ethyl 4-hydroxy-1-methylbicyclo[3.1.0]hexane-2-carboxylate

HRID 1854317Notes

Reaction equation

HRID 1854317 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][C@@H:9]([OH:11])[CH:8]=[C:7]1[CH3:12])=[O:5])[CH3:2].Cl[CH2:14]I>>[OH:11][C@H:9]1[C@@H:8]2[C@@:7]([CH3:14])([CH2:12]2)[C@@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:10]1.[OH:11][C@@H:9]1[C@H:8]2[C@:7]([CH3:14])([CH2:12]2)[C@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:10]1

Participants

4

Reactant 2

HCID 11644ChloroiodomethaneHCID 10877556cis-Ethyl 4-hydroxy-2-methylcyclopent-2-enecarboxylate

Product 2

HCID 58010081(1S,2R,4S,5R)-ethyl 4-hydroxy-1-methylbicyclo[3.1.0]hexane-2-carboxylateYield 113.6%HCID 58010225(1R,2S,4R,5S)-ethyl 4-hydroxy-1-methylbicyclo[3.1.0]hexane-2-carboxylate

Procedure

cis-Ethyl-4-hydroxy-2-methylcyclopent-2-enecarboxylate (0.96 g, 5.64 mmol, Preparation #MM.1) and chloroiodomethane (4.97 g, 28.2 mmol) were reacted according to General Procedure KK to give (1R,2S,4R,5S)-ethyl 4-hydroxy-1-methylbicyclo[3.1.0]hexane-2-carboxylate and (1S,2R,4S,5R)-ethyl 4-hydroxy-1-methylbicyclo[3.1.0]hexane-2-carboxylate (0.59 g, 57%) after purification by flash silica gel chromatography eluting with a gradient of 30-60% EtOAc/heptane: 1H NMR (400 MHz, CDCl3) δ 4.60-4.51 (m, 1H), 4.23-4.10 (m, 2H), 2.74 (dd, J=8.0, 10.9 Hz, 1H), 2.13 (m, 1H), 1.51 (m, 1H), 1.46-1.40 (m, 1H), 1.35-1.29 (m, 1H), 1.28 (m, 6H), 1.09-1.04 (m, 1H), 0.37 (dd, J=5.7, 7.9 Hz, 1H).

Sources & evidence

ORD record
ord-9b22c3469fc8429ab72e879ef2134c54
Source dataset
uspto-grants-2015_02
Patent number
US08962629B2

Reaction notes

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