Sodium cyanoborohydride → HCID 22036775, compound

HRID 1789978Notes

Reaction equation

HRID 1789978 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:24][CH2:23][C:9]2[N:10]3[C:19]4[C:18]([C:8]=2[CH2:7]1)=[CH:17][CH:16]=[CH:15][C:14]=4[N:13]([CH3:20])[CH2:12][C:11]3([CH3:22])[CH3:21])=[O:5])[CH3:2].[BH3-]C#N.[Na+]>C(O)(C(F)(F)F)=O>[CH2:1]([O:3][C:4]([N:6]1[CH2:24][CH2:23][CH:9]2[N:10]3[C:19]4[C:18]([CH:8]2[CH2:7]1)=[CH:17][CH:16]=[CH:15][C:14]=4[N:13]([CH3:20])[CH2:12][C:11]3([CH3:21])[CH3:22])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 22036817HCID 22036817, compound

Product 1

HCID 22036775HCID 22036775, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of ethyl-1,1,3-trimethyl-2,3,9,10-tetrahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate (69 mg, 0.21 mmol) in TFA (2 mL) at 0° C. was added NaBH3CN (53 mg, 0.84 mmol). The mixture was stirred at rt for 4 hours, and then removed the TFA by N2. About 10 mL of H2O was added and then was extracted with EtOAc (2×10 mL). The combined extracts were dried over magnesium sulfate and concentrated to afford ethyl-1,1,3-trimethyl-2,3,6b,9,10,10a-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline-8(7H)-carboxylate as an oil which was used for the next reaction (45 mg, 65%). MS [M+H]+ 330.

Workup

  1. customremoved the TFA by N2
  2. additionAbout 10 mL of H2O was added
  3. extractionwas extracted with EtOAc (2×10 mL)
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-839480f60904490981a35ec588a9f443
Source dataset
uspto-grants-2006_07
Patent number
US07071186B2

Reaction notes

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