Hydrochloric Acid → (R)-5-Amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 1864828Notes

Reaction equation

HRID 1864828 reaction equation
[O:1]=[C:2]1[N:10](COCC[Si](C)(C)C)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@:3]21[CH2:26][C:25]1[C:20](=[CH:21][CH:22]=[C:23]([NH:27]C(=O)OC(C)(C)C)[CH:24]=1)[CH2:19]2.Cl.C(N)CN.[OH-].[Na+]>CO.O>[NH2:27][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[CH2:19][C@:3]1([C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:10][C:2]1=[O:1])[CH2:26]2

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 3301EthylenediamineHCID 14798Sodium HydroxideHCID 73013404(R)-tert-butyl 2'-oxo-1'-((2-(trimethylsilyl)ethoxy)methyl)-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridine]-5-ylcarbaMate

Product 1

HCID 53260812(R)-5-Amino-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of tert-butyl (R)-(2′-oxo-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-yl)carbamate from Step C (13.4 g, 27.8 mmol) in MeOH (300 mL) was saturated with HCl (g). The mixture was resaturated with HCl (g) every 30 min until the starting material was consumed, and then concentrated in vacuo. The residue was dissolved in MeOH (150 mL) and treated with ethylenediamine (1.9 mL, 27.8 mmol) and 10 N sodium hydroxide (6 mL, 60 mmol) to adjust the mixture to pH 10. After 30 min, the mixture was diluted with H2O (400 mL) and extracted with CHCl3 (1 L). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude material was triturated with MeOH (35 mL) to give the title compound. MS: m/z=252 (M+1).

Workup

  1. customwas consumed
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in MeOH (150 mL)
  4. extractionextracted with CHCl3 (1 L)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude material was triturated with MeOH (35 mL)

Sources & evidence

ORD record
ord-91ec8a271a7f4a2a8cda529725fd9b3b
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Reaction notes

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