tert-Butanol → Ammonium Hydroxide

HRID 1685391ノート

反応式

HRID 1685391 の反応式
[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=[N:14][C:15](C(O)=O)=[CH:16][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=[N:14][C:15]([NH:24][C:27](=[O:36])[O:50][C:46]([CH3:49])([CH3:48])[CH3:47])=[CH:16][CH:17]=[C:12]1[CH2:11]2

参加物

6

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 57974096(+/-)-2'-Oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridine]-2-carboxylic acid

生成物 2

HCID 14923Ammonium HydroxideHCID 86616405(+/-)-tert-Butyl (2'-oxo-1',2',5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-2-yl)carbamate

実験手順

To a suspension of (±)-2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridine]-2-carboxylic acid from Step E (224 mg, 0.796 mmol) and triethylamine (0.333 mL, 2.39 mmol) in tert-butanol (5 mL) was added diphenylphosphoryl azide (0.258 mL, 1.20 mmol) and the mixture was heated at reflux for 1 h. The reaction mixture was concentrated in vacuo and then partitioned between CH2Cl2 (20 mL) and saturated NaHCO3 (20 mL). The organic layer was separated and the aqueous layer was further extracted with CH2Cl2 (2×20 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).

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompartitioned between CH2Cl2 (20 mL) and saturated NaHCO3 (20 mL)
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was further extracted with CH2Cl2 (2×20 mL)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by silica gel chromatography
  11. washeluting with a gradient of CH2Cl2

出典と根拠

ORDレコード
ord-60870fad1c2a44598b5727a9fb61f4b0
出典データセット
uspto-grants-2012_04
特許番号
US08148390B2

反応ノート

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