tert-Butanol → Ammonium Hydroxide

HRID 552560Notes

Reaction equation

HRID 552560 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]21[CH2:21][C:13]1[CH:14]=[N:15][C:16](C(O)=O)=[CH:17][C:12]=1[CH2:11]2.C([N:24]([CH2:27]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1.[C:46]([OH:50])([CH3:49])([CH3:48])[CH3:47]>>[NH4+:6].[OH-:1].[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]21[CH2:21][C:13]1[CH:14]=[N:15][C:16]([NH:24][C:27](=[O:36])[O:50][C:46]([CH3:49])([CH3:48])[CH3:47])=[CH:17][C:12]=1[CH2:11]2

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 57974027(+/-)-2'-Oxo-1',2',5,7-tetrahydrospiro[cyclopenta[c]pyridine-6,3'-pyrrolo[2,3-b]pyridine]-3-carboxylic acid2×

Product 2

HCID 14923Ammonium HydroxideHCID 86616403(+/-)-Tert-butyl(2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[c]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-3-yl)carbamate

Procedure

To a refluxing suspension of (±)-2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[c]pyridine-6,3′-pyrrolo[2,3-b]pyridine]-3-carboxylic acid (200 mg, 0.711 mmol, described in Intermediate 5) and triethylamine (0.149 mL, 1.07 mmol) in tert-butanol (10 mL) was added diphenylphosphoryl azide (0.184 mL, 0.853 mmol). After 18 h at reflux, the mixture was concentrated in vacuo. The residue was partitioned between CH2Cl2 (50 mL) and saturated NaHCO3 (30 mL) The organic layer was separated and the aqueous layer was further extracted with CH2Cl2 (2×50 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH: NH4OH-100:0:0 to 95:5:1, to give the title compound. MS: m/z=353 (M+1).

Workup

  1. temperatureAfter 18 h at reflux
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was partitioned between CH2Cl2 (50 mL) and saturated NaHCO3 (30 mL) The organic layer
  4. customwas separated
  5. extractionthe aqueous layer was further extracted with CH2Cl2 (2×50 mL)
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by silica gel chromatography
  10. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-141ade0923294d66b78c7e6b17e35557
Source dataset
uspto-grants-2011_05
Patent number
US07951795B2

Reaction notes

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