Methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[3.3]hept-5-ene-2-carboxylate → HCID 86692402, compound

HRID 1401040Notes

Reaction equation

HRID 1401040 reaction equation
[CH3:1][C:2]1([CH3:20])[C:6]([CH3:8])([CH3:7])[O:5][B:4](C2CC3(CC(C(OC)=O)C3)C=2)[O:3]1.[C:21]([NH:24][C:25]1([C:39]([O:41][CH3:42])=[O:40])[CH2:30][CH2:29][C:28](OS(C(F)(F)F)(=O)=O)=[CH:27][CH2:26]1)(=[O:23])[CH3:22]>>[C:21]([NH:24][C:25]1([C:39]([O:41][CH3:42])=[O:40])[CH2:30][CH2:29][C:28]([B:4]2[O:5][C:6]([CH3:8])([CH3:7])[C:2]([CH3:20])([CH3:1])[O:3]2)=[CH:27][CH2:26]1)(=[O:23])[CH3:22]

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 86692399Methyl 1-acetamido-4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-enecarboxylate

Product 1

HCID 86692402HCID 86692402, compoundYield 48.4%

Procedure

The title compound was prepared 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 methyl 1-acetamido-4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-enecarboxylate as the reactant. (48.4% yield). MS: m/e 325.25 (M+H)+, 2.126 min (method 8). 1H NMR (400 MHz, CHLOROFORM-d) δ 6.42 (br. s., 1H), 5.90 (s, 1H), 3.83-3.59 (m, 3H), 2.65 (d, J=18.8 Hz, 1H), 2.35 (d, J=18.1 Hz, 1H), 2.25 (d, J=11.0 Hz, 2H), 2.13-2.03 (m, 1H), 1.98-1.90 (m, 3H), 1.88-1.75 (m, 1H), 1.36-1.18 (m, 12H).

Workup

  1. customm/e 325.25 (M+H)+, 2.126 min (method 8)

Sources & evidence

ORD record
ord-8fe78f38702540beb1681fa97aa0c2de
Source dataset
uspto-grants-2014_12
Patent number
US08906889B2

Reaction notes

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