Sodium Carbonate → Tert-butyl (5-(cyclopent-1-en-1-yl)-2-nitrophenyl)carbamate

HRID 62676Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7](B2OC(C)(C)C(C)(C)O2)=[CH:6][C:5]=1[NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])([O-:3])=[O:2].FC(F)(F)S(O[C:33]1[CH2:37][CH2:36][CH2:35][CH:34]=1)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:33]1([C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH:6]=2)[CH2:37][CH2:36][CH2:35][CH:34]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of tert-butyl (2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate (16 g, 43.9 mmol, 1.0 equiv.) in 1,4-dioxane (320 mL) were added cyclopent-1-en-1-yl trifluoromethanesulfonate (11.4 g, 52.7 mmol, 1.2 equiv.), Pd (PPh3)4 (2.54 g, 2.2 mmol, 0.05 equiv.) and a solution of Na2CO3 (5.6 g, 52.7 mmol, 1.2 equiv.) in water (160 mL) at room temperature. The reaction was then heated to 110° C. and stirred for 4 h. The reaction mixture was filtered through celite then concentrated under reduced pressure. The crude residue was purified by column chromatography (silica gel, 2% EtOAc/hexanes) to give tert-butyl (5-(cyclopent-1-en-1-yl)-2-nitrophenyl)carbamate (4.3 g, 32% yield).

Workup

customat room temperature
filtrationThe reaction mixture was filtered through celite
concentrationthen concentrated under reduced pressure
customThe crude residue was purified by column chromatography (silica gel, 2% EtOAc/hexanes)

Sources & evidence

ORD record: ord-36afe7f4d615446bac3598434a8cfca6
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447030B2

Reaction notes

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