Lithium borohydride → tert-butyl 1-(2-(4-chlorophenyl)-1-hydroxybutan-2-yl)-1H-indazol-4-ylcarbamate

HRID 1427227ノート

反応式

HRID 1427227 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[N:12][N:13]2[C:18]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)([CH2:23][CH3:24])[C:19](OC)=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[BH4-]>C1COCC1>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([C:18]([N:13]2[C:14]3[C:10](=[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:17]=[CH:16][CH:15]=3)[CH:11]=[N:12]2)([CH2:23][CH3:24])[CH2:19][OH:20])=[CH:26][CH:27]=1

参加物

4

反応物 2

HCID 4148881Lithium borohydrideHCID 70562967methyl 2-(4-(tert-butoxycarbonylamino)-1H-indazol-1-yl)-2-(4-chlorophenyl)butanoate

生成物 1

HCID 70560487tert-butyl 1-(2-(4-chlorophenyl)-1-hydroxybutan-2-yl)-1H-indazol-4-ylcarbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 2-[4-(tert-butoxycarbonylamino)-1H-indazol-1-yl]-2-(4-chlorophenyl)butanoate (3.5 g, 7.90 mmol), in THF (140 mL) at 0° C. was added LiBH4 (0.7 g, 31.6 mmol). The mixture was allowed to stir overnight at RT. Then it was quenched with saturated NH4Cl (200 mL) carefully, and extracted with CH2Cl2. The combined organic layers were washed with brine (80 mL), dried over anhydrous sodium sulfate, filtered and the solvent was removed in vacuo to afford the desired product. LC/MS m/z=416.3 [M+H]+.

後処理

  1. customThen it was quenched with saturated NH4Cl (200 mL) carefully
  2. extractionextracted with CH2Cl2
  3. washThe combined organic layers were washed with brine (80 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-6b73678f68e5425db4787d3635728406
出典データセット
uspto-grants-2015_01
特許番号
US08933113B2

反応ノート

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