Hydrochloric Acid → HCID 68690971, compound

HRID 1159117Notes

Reaction equation

HRID 1159117 reaction equation
C(OC([N:8]1[CH2:28][CH2:27][N:11]2[C:12](=[O:26])[C:13]3[CH:14]=[C:15]([C:22]([F:25])([F:24])[F:23])[CH:16]=[C:17]([CH2:20][CH3:21])[C:18]=3[CH2:19][C@@H:10]2[CH2:9]1)=O)(C)(C)C.[ClH:29].O1CCOCC1.C(OCC)C>CCO.[Pd]>[ClH:29].[CH2:20]([C:17]1[C:18]2[CH2:19][C@@H:10]3[CH2:9][NH:8][CH2:28][CH2:27][N:11]3[C:12](=[O:26])[C:13]=2[CH:14]=[C:15]([C:22]([F:23])([F:25])[F:24])[CH:16]=1)[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 312751,4-DioxaneHCID 68692766HCID 68692766, compound

Product 1

HCID 68690971HCID 68690971, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

MS (ESI) 340 (M+H). Crude (R)-2-N-(t-butoxycarbonyl)-10-ethyl-8-trifluoromethyl-1,2,3,4,11,11a-hexahydropyrazino[1,2-b]isoquinolin-6-one was dissolved in EtOH (2 mL) and hydrogenated [10% Pd/C (50 mg), H2 (30 psi)]. The reaction mixture was filtered through diatomaceous earth, and then purified by flash column chromatography (silica gel, 4:1 hexanes/EtOAc). The resulting material was deprotected using 4 N HCl in 1,4-dioxane (200 μL, 0.8 mmol), followed by trituration with diethyl ether, to provide the desired product (18 mg, 40% over 3 steps) as a white solid. MS (ESI) 299 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. custompurified by flash column chromatography (silica gel, 4:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-afc75c0d363c4a0f91eb5d26df00b1d0
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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