Acetic Acid → HCID 131724529, compound

HRID 1836563Notes

Reaction equation

HRID 1836563 reaction equation
[ClH:1].Cl.[CH:3]1[CH:12]=[CH:11][C:10]2[CH2:13][CH2:14][CH2:15][N:8]3[C:9]=2[C:4]=1[C@@H:5]1[CH2:18][NH:17][CH2:16][C@H:6]1[CH2:7]3.C=O.[C:21](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.Cl>ClCCCl.CCOCC>[ClH:1].[ClH:1].[CH3:21][N:17]1[CH2:18][C@@H:5]2[C@H:6]([CH2:7][N:8]3[CH2:15][CH2:14][CH2:13][C:10]4[CH:11]=[CH:12][CH:3]=[C:4]2[C:9]3=4)[CH2:16]1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 131724530HCID 131724530, compound

Product 1

HCID 131724529HCID 131724529, compoundYield 52.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of (±)-trans-5,6,8,8a,9,10,11,11a-octahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline from EXAMPLE 4 (95 mg, 0.44 mmol) in 5 mL of 1,2-dichloroethane was added 37% aqueous formaldehyde (0.043 mL, 0.53 mmol), sodium triacetoxyborohydride (168 mg, 0.79 mmol) and glacial acetic acid (0.027 mL, 0.48 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 (0.44 mL, 0.88 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 35 mg (27%) of the title compound of EXAMPLE 6 as an off white powder. 1H NMR (d6-dmso): δ 11.22 (broad s, 1H), 6.76 (d, 1H, J=7.7 Hz), 6.57 (dd, 1H, J=7.3, 12.5 Hz), 6.38 (t, 1H, J=7.3 Hz), 4.17-4.08 (m, 1H), 3.81-3.72 (m, 1H), 3.68-3.60 (m, 1H), 3.42-3.18 (m, 5H), 2.98-2.80 (m, 4H), 2.66-2.60 (m, 2H), 2.10-1.98 (m, 1H), 1.95-1.83 (m, 1H), 1.82-1.72 (m, 1H). LRMS (ES)+: 229.4 (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-1c4508d39ef241ea8f575b43257b48b3
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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