Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[3.3]hept-5-ene-2-carboxylate → Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bicyclo[3.1.0]hex-2-ene-6-carboxylate

HRID 1401028Notes

Reaction equation

HRID 1401028 reaction equation
[CH3:1][C:2]1([CH3:20])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH2:19][C:11]3([CH2:14][CH:13]([C:15]([O:17][CH3:18])=[O:16])C3)[CH:10]=2)[O:3]1.F[C:22](F)(F)S(OC1C[C@H]2[C@H]([C@@H]2C(OCC)=O)C=1)(=O)=O>>[CH3:7][C:6]1([CH3:8])[C:2]([CH3:1])([CH3:20])[O:3][B:4]([C:9]2[CH2:19][CH:11]3[CH:14]([CH:13]3[C:15]([O:17][CH2:18][CH3:22])=[O:16])[CH:10]=2)[O:5]1

Participants

3

Reactant 2

HCID 86692319Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[3.3]hept-5-ene-2-carboxylateHCID 86692389(+/-)-(1S,5S,6R)-ethyl 3-(((trifluoromethyl)sulfonyl)oxy)bicyclo[3.1.0]hex-2-ene-6-carboxylate

Product 1

HCID 86692388Ethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)bicyclo[3.1.0]hex-2-ene-6-carboxylate

Procedure

The title compound was prepared in quantitative yield following the method described in step 2 for the preparation of methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[3.3]hept-5-ene-2-carboxylate, using (±)-(1S,5S,6R)-ethyl 3-(((trifluoromethyl)sulfonyl)oxy)bicyclo[3.1.0]hex-2-ene-6-carboxylate as the reactant. 1H NMR (500 MHz, CHLOROFORM-d) δ 6.67 (q, J=2.0 Hz, 1H), 4.27-3.98 (m, 2H), 2.89-2.72 (m, 1H), 2.63-2.53 (m, 1H), 2.54-2.41 (m, 1H), 2.28 (td, J=6.2, 3.3 Hz, 1H), 1.33-1.15 (m, 16H).

Sources & evidence

ORD record
ord-cca6ad00d4d44e97ae0c4e4cf9af581d
Source dataset
uspto-grants-2014_12
Patent number
US08906889B2

Reaction notes

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