Diisopropylethylamine → 1-tert-Butyl 8-(2,5-dioxopyrrolidin-1-yl) octanedioate

HRID 535284Notes

Reaction equation

HRID 535284 reaction equation
[C:1]([O:5][C:6](=[O:16])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])([CH3:4])([CH3:3])[CH3:2].[B-](F)(F)(F)F.CN(C(O[N:30]1[C:35](=[O:36])[CH2:34][CH2:33][C:31]1=[O:32])=[N+](C)C)C.CCN(C(C)C)C(C)C>C1COCC1>[O:32]=[C:31]1[CH2:33][CH2:34][C:35](=[O:36])[N:30]1[O:14][C:13](=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:16]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 214648798-(tert-Butoxy)-8-oxooctanoic acid

Product 1

HCID 597608961-tert-Butyl 8-(2,5-dioxopyrrolidin-1-yl) octanedioate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Octanedioic acid mono-tert-butyl ester (3.14 g, 13.63 mmol) was dissolved in THF (100 mL). TSTU (4.9 g, 16.3 mmol) was added and pH was adjusted to 8.5 with DIPEA (2.85 mL).

Sources & evidence

ORD record
ord-a873739603384a40b721c7b748660e73
Source dataset
uspto-grants-2014_10
Patent number
US08859493B2

Reaction notes

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