Diisopropylethylamine → 4-[[(7aS)-2-(2-bromophenyl)-hexahydro-1-oxo-3H-pyrrolo[1,2-c]imidazol-3-ylidene]amino]-3-hydroxybenzonitrile

HRID 413344Notes

Reaction equation

HRID 413344 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]=[C:10]=[N:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Br:18])=[C:5]([O:19][Si](C(C)(C)C)(C)C)[CH:4]=1)#[N:2].C(N(C(C)C)CC)(C)C.Cl.C([O:44][C:45](=O)[C@@H:46]1[CH2:50][CH2:49][CH2:48][NH:47]1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CO>[Br:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N:11]1[C:45](=[O:44])[C@@H:46]2[CH2:50][CH2:49][CH2:48][N:47]2[C:10]1=[N:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[OH:19]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724141Tetrabutylammonium FluorideHCID 2733413Proline benzyl ester hydrochlorideHCID 12043083N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N'-(2-bromophenyl)carbodiimide

Product 1

HCID 99314144-[[(7aS)-2-(2-bromophenyl)-hexahydro-1-oxo-3H-pyrrolo[1,2-c]imidazol-3-ylidene]amino]-3-hydroxybenzonitrileYield 67.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The standard procedure was followed using N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N′-(2-bromophenyl)carbodiimide (54 mg, 0.13 mmol), diisopropylethylamine (32 μL, 0.29 mmol), L-proline benzylester hydro chloride (34 mg, 0.14 mmol) and TBAF (0.16 mL, 0.16 mmol) in THF (2 mL) and methanol (0.1 mL) to give 36 mg (67%) of 4-[[(7aS)-2-(2-bromophenyl)-hexahydro-1-oxo-3H-pyrrolo[1,2-c]imidazol-3-ylidene]amino]-3-hydroxybenzonitrile as a tan powder. 1H NMR (400 MHz, MeOD) δ 7.6 (2H, m), 7.35 (3H, m), 7.15 (1H, m), 7.0 (1H, m), 4.5 (1H, t), 3.0 (1H, m), 2.4 (1H, m), 2.2 (1H, m), 2.05 (2H, m); MS(EI) m/e 412 (M+).

Sources & evidence

ORD record
ord-8a6ad24cf5f943f6a440cecc0e1b877d
Source dataset
uspto-grants-2003_05
Patent number
US06566387B1

Reaction notes

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