Sodium borohydride → (S)-2-(Hydroxymethyl)-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 1623068ノート

反応式

HRID 1623068 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]=[C:18]([CH:22]=[O:23])[CH:17]=[CH:16]3.[BH4-].[Na+]>CO.CS(C)=O>[OH:23][CH2:22][C:18]1[CH:17]=[CH:16][C:15]2[C:20](=[CH:21][C:12]3[CH2:11][C@:3]4([C:4]5[C:5](=[N:6][CH:7]=[CH:8][CH:9]=5)[NH:10][C:2]4=[O:1])[CH2:24][C:13]=3[CH:14]=2)[N:19]=1

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 59594285(S)-2'-Oxo-1',2',6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridine]-2-carbaldehyde2 回

生成物 1

HCID 67016575(S)-2-(Hydroxymethyl)-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 887Methanol溶媒

実験手順

To a stirred suspension of (S)-2′-oxo-1′,2′,6,8-tetrahydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridine]-2-carbaldehyde (80 mg, 025 mmol, described in Intermediate 6) in a mixture of MeOH (5 mL) and DMSO (1 mL) was added sodium borohydride (19 mg, 0.51 mmol). The resulting mixture was stirred at ambient temperature for 1 h, then the MeOH was removed in vacuo. The residue was partitioned between saturated aqueous NaHCO3 (20 mL) and CH2Cl2 (20 mL). The aqueous layer was extracted further with CH2Cl2 (2×20 mL). The combined organic extracts were dried over Na2—SO4, filtered, and concentrated in vacuo to give the title compound in sufficient purity for use in the next step. MS: m/z=318 (M+1).

後処理

  1. customthe MeOH was removed in vacuo
  2. customThe residue was partitioned between saturated aqueous NaHCO3 (20 mL) and CH2Cl2 (20 mL)
  3. extractionThe aqueous layer was extracted further with CH2Cl2 (2×20 mL)
  4. dry with materialThe combined organic extracts were dried over Na2—SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-75b06855600944908b988edaa54d362f
出典データセット
uspto-grants-2014_07
特許番号
US08778957B2

反応ノート

読み込み中…