Hydrochloric Acid → HCID 66875593, compound

HRID 2079822Notes

Reaction equation

HRID 2079822 reaction equation
C(OC([N:8]1[CH2:12][CH:11]2[CH2:13][N:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][N:17]=3)[CH2:15][CH:10]2[CH2:9]1)=O)(C)(C)C.[ClH:27].O1CCOCC1>CCOCC>[ClH:27].[CH2:13]1[CH:11]2[CH2:12][NH:8][CH2:9][CH:10]2[CH2:15][N:14]1[C:16]1[CH:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59367625HCID 59367625, compound

Product 1

HCID 66875593HCID 66875593, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To ethyl 2-[5-(tert-butoxycarbonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]pyridine-5-carboxylate (1.429 g, 3.92 mmol) was added 4M HCl in dioxane (10 ml, 40 mmol). The mixture was stirred for 2 h, then Et2O (50 ml) was added. The product was collected by filtration and washed with further Et2O (50 ml) to yield the title compound (1.19 g, quant.). 1H NMR (300 MHz, d6-DMSO) δ: 9.95 (1H, br s), 9.84 (1H, br s), 8.44 (1H, d, J=1.8 Hz), 8.20 (1H, dd, J=2.1, 9.3 Hz), 7.01 (1H, d, J=9.3 Hz), 4.31 (2H, q, J=7.2 Hz), 3.0-4.05 (10H, m), 1.31 (3H, t, J=7.2 Hz).

Workup

  1. filtrationThe product was collected by filtration
  2. washwashed with further Et2O (50 ml)

Sources & evidence

ORD record
ord-3cdb33e9e50d4e11bd5eada733f63a1c
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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