Hydrochloric Acid → HCID 131724547, compound

HRID 1836587Notes

Reaction equation

HRID 1836587 reaction equation
[ClH:1].Cl.[CH:3]1[CH:12]=[CH:11][C:10]2[CH2:13][CH2:14][N:8]3[C:9]=2[C:4]=1[C@H:5]1[CH2:17][NH:16][CH2:15][C@H:6]1[CH2:7]3.C=O.[C:20](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl>ClCCCl.CCOCC>[ClH:1].[ClH:1].[CH3:20][N:16]1[CH2:17][C@H:5]2[C@H:6]([CH2:7][N:8]3[CH2:14][CH2:13][C:10]4[CH:11]=[CH:12][CH:3]=[C:4]2[C:9]3=4)[CH2:15]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 131724545HCID 131724545, compound

Product 1

HCID 131724547HCID 131724547, compoundYield 99.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (±)-cis-4,5,7,7a,8,9,10,10a-octahydrodipyrrolo[3,4-c:3′,2′,1′-ij]quinoline free base from EXAMPLE 109 (140 mg, 0.70 mmol) in 10 mL of 1,2-dichloroethane was added 37% aqueous formaldehyde (0.125 mL, 1.4 mmol) and sodium triacetoxyborohydride (0.45 g, 2.1 mmol). The resulting mixture was stirred at ambient temperature for 1 h and then the reaction was quenched with water. The mixture was partitioned between chloroform and saturated aqueous sodium carbonate. The organics were washed with brine, dried (K2CO3) and concentrated in vacuo. The residue was dissolved in 1 mL ethanol and 5 mL of ether and then there was added 2M HCl in ether (1.05 mL, 2.1 mmol). A solid precipitated out of solution. The solvents were decanted and the solid was triturated twice with ether and dried in vacuo to afford 100 mg (50%) of the title compound of EXAMPLE 110 as an off white powder LRMS (ES)+: 214.9 (M+H)+.

Workup

  1. customthe reaction was quenched with water
  2. customThe mixture was partitioned between chloroform and saturated aqueous sodium carbonate
  3. washThe organics were washed with brine
  4. dry with materialdried (K2CO3)
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in 1 mL ethanol
  7. customA solid precipitated out of solution
  8. customThe solvents were decanted
  9. customthe solid was triturated twice with ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-540520d1928b47c187291ee4e27a2239
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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