1,1-Cyclobutanedicarboxylic acid → HCID 56995940, compound

HRID 1245561Notes

Reaction equation

[C:1]1([C:8]([OH:10])=[O:9])([C:5]([OH:7])=O)[CH2:4][CH2:3][CH2:2]1.C(N([CH2:16][CH3:17])CC)C.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CN([CH:29]=[O:30])C>>[C:1]1([C:5]([O:30][CH2:29][C:17]2[CH:16]=[CH:3][CH:2]=[CH:1][CH:4]=2)=[O:7])([C:8]([O:10][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:9])[CH2:2][CH2:3][CH2:4]1

Participants

Reactant 4

HCID 25681,1-Cyclobutanedicarboxylic acid

HCID 6228Dimethylformamide

HCID 7498Benzyl Bromide

HCID 8471Triethylamine

Product 1

HCID 56995940HCID 56995940, compound

Procedure

A solution of 2.0 g (13.8 mmol) of cyclobutanedicarboxylic acid in 20 mL of DMF at 0° C. was treated with 7.7 mL (55.5 mmol) of triethylamine and 5.0 mL (41.6 mmol) of benzyl bromide. The reaction was warmed to rt and stirred overnight. The reaction was partitioned between H2O and CH2Cl2. The residue was purified with a 40M Biotage column using 1:1 v/v of hexanes/EtOAc as the eluant to afford the title compound: 1H-NMR (500 MHz) δ 1.95–2.03 (m, 2H), 2.55–2.58 (m, 4H), 5.14 (s, 4H), 7.24–7.37 (m, 10H).

Workup

customThe reaction was partitioned between H2O and CH2Cl2
customThe residue was purified with a 40M Biotage column

Sources & evidence

ORD record: ord-a2c1b620bf444e5eb0b79c166c12a45d
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07125887B2

Reaction notes

Loading…