Sodium borohydride → Ammonium Hydroxide

HRID 1890701ノート

反応式

HRID 1890701 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[CH2:24][C:13]1[CH:14]=[C:15]3[C:20](=[CH:21][C:12]=1[CH2:11]2)[N:19]=[CH:18][C:17]([CH:22]=[O:23])=[CH:16]3.[BH4-].[Na+]>CO.C(Cl)Cl>[NH4+:6].[OH-:1].[OH:23][CH2:22][C:17]1[CH:18]=[N:19][C:20]2[C:15]([CH:16]=1)=[CH:14][C:13]1[CH2:24][C@:3]3([CH2:11][C:12]=1[CH:21]=2)[C:4]1[C:5](=[N:6][CH:7]=[CH:8][CH:9]=1)[NH:10][C:2]3=[O:1]

参加物

6

反応物 2

HCID 4311764Sodium borohydride2 回HCID 59594304HCID 59594304、化合物2 回

生成物 2

HCID 14923Ammonium HydroxideHCID 58550612(3′S)-6,8-Dihydro-3-(hydroxymethyl)spiro[7H-cyclopenta[g]quinoline-7,3′-[3H]pyrrolo[2,3-b]pyridin]-2′(1′H)-one

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

To a stirred suspension of (7S)-2′-oxo-1′,2′,6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridine]-3-carbaldehyde (1.79 g, 5.68 mmol, described in Intermediate 1) in a mixture of MeOH (30 mL) and CH2Cl2 (10 mL) was added sodium borohydride (322 mg, 8.52 mmol). The resulting mixture was stirred at ambient temperature for 48 h, with additional sodium borohydride (322 mg, 8.52 mmol) added at 16 and 20 h. The solvents were removed in vacuo and the residue was partitioned between saturated aqueous NaHCO3 (100 mL) and CH2Cl2 (100 mL). The aqueous layer was extracted further with CH2Cl2 (2×100 mL). The combined organic extracts 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=318 (M+1).

後処理

  1. additionadded at 16 and 20 h
  2. customThe solvents were removed in vacuo
  3. customthe residue was partitioned between saturated aqueous NaHCO3 (100 mL) and CH2Cl2 (100 mL)
  4. extractionThe aqueous layer was extracted further with CH2Cl2 (2×100 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with a gradient of CH2Cl2

出典と根拠

ORDレコード
ord-54fce952ab33439ebb584be363d3dd40
出典データセット
uspto-grants-2013_08
特許番号
US08507477B2

反応ノート

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