1,3-Dihydro-5-nitro-1'-((2-(trimethylsilyl)ethoxy)methyl)spiro(2H-indene-2,3'-(3H)pyrrolo(2,3-b)pyridin)-2'(1'H)-one → (S)-5-Amino-1'-((2-(trimethylsilyl)ethoxy)methyl)-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'h)-one

HRID 550971ノート

反応式

HRID 550971 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:27](=[CH:28][CH:29]=1)[CH2:26][C:8]1([C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:24])([CH3:23])[CH3:22])[C:9]1=[O:25])[CH2:7]2)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:27](=[CH:28][CH:29]=1)[CH2:26][C@@:8]1([C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][O:18][CH2:19][CH2:20][Si:21]([CH3:22])([CH3:23])[CH3:24])[C:9]1=[O:25])[CH2:7]2

参加物

4

反応物 1

HCID 591667381,3-Dihydro-5-nitro-1'-((2-(trimethylsilyl)ethoxy)methyl)spiro(2H-indene-2,3'-(3H)pyrrolo(2,3-b)pyridin)-2'(1'H)-one

生成物 1

HCID 67016448(S)-5-Amino-1'-((2-(trimethylsilyl)ethoxy)methyl)-1,3-dihydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'h)-one

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A mixture of 10% Pd/C (3 g) and (±)-5-nitro-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1H)-one from Step A (19.1 g, 46.4 mmol) was stirred vigorously in EtOH (400 mL) under an atmosphere of hydrogen (ca. 1 atm). After 18 h, the mixture was filtered through a pad of Celite, washing extensively with MeOH, and the filtrate was concentrated in vacuo to give the crude racemic compound. The enantiomers were resolved by HPLC, utilizing a Chiralcel OD column and eluting with MeOH. The first major peak to elute was (S)-5-amino-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one, the title compound, and the second major peak to elute was (R)-5-amino-1′-{[2-(trimethylsilyl)ethoxy]methyl}-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one. MS: m/z=382 (M+1).

後処理

  1. filtrationthe mixture was filtered through a pad of Celite
  2. washwashing extensively with MeOH
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto give the crude racemic compound
  5. washeluting with MeOH
  6. washThe first major peak to elute
  7. washthe title compound, and the second major peak to elute

出典と根拠

ORDレコード
ord-c03ec81cc9604534b31762ee8bf97573
出典データセット
uspto-grants-2011_05
特許番号
US07947677B2

反応ノート

読み込み中…