Lithium Chloride → tert-Butyl (2S,4S)-2-(hydroxymethyl)-4-{[(1-isopropyl-1H-indazol-3-yl)carbonyl]amino}pyrrolidine-1-carboxylate

HRID 602467ノート

反応式

HRID 602467 の反応式
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:13]([NH:15][C@@H:16]2[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C@H:18]([C:28](OC)=[O:29])[CH2:17]2)=[O:14])=[N:5]1)([CH3:3])[CH3:2].[Cl-].[Li+].[BH4-].[Na+]>O1CCCC1CO>[OH:29][CH2:28][C@@H:18]1[CH2:17][C@H:16]([NH:15][C:13]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:4]([CH:1]([CH3:2])[CH3:3])[N:5]=2)=[O:14])[CH2:20][N:19]1[C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22]

参加物

5

反応物 3

HCID 433294Lithium Chloride2 回HCID 4311764Sodium borohydride2 回HCID 866241491-tert-Butyl 2-methyl (2S,4S)-4-{[(1-isopropyl-1H-indazol-3-yl)carbonyl]amino}pyrrolidine-1,2-dicarboxylate

生成物 1

HCID 67270520tert-Butyl (2S,4S)-2-(hydroxymethyl)-4-{[(1-isopropyl-1H-indazol-3-yl)carbonyl]amino}pyrrolidine-1-carboxylate収率 93%

試薬・触媒・溶媒 1

HCID 7360Tetrahydrofurfuryl alcohol溶媒

実験手順

To a stirred solution of 1-tert-butyl 2-methyl (2S,4S)-4-{[(1-isopropyl-1H-indazol-3-yl)carbonyl]amino}pyrrolidine-1,2-dicarboxylate (135 mg, 0.313 mmol, step 1 of Example 7) in tetrahydrofuran-methanol (2 mL-2 mL) were added lithium chloride (81 mg, 1.92 mmol) and sodium borohydride (73 mg, 1.92 mmol) at room temperature. The resulting mixture was stirred at the same temperature for 20 h. Another lithium chloride (81 mg, 1.92 mmol) and sodium borohydride (73 mg, 1.92 mmol) were added to the mixture at room temperature. After stirring for 3 h, the mixture was quenched with water (10 mL), extracted with ethyl acetate (100 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (1:1) to give 117 mg (93%) of the title compound as a colorless oil.

後処理

  1. stirringAfter stirring for 3 h
  2. customthe mixture was quenched with water (10 mL)
  3. extractionextracted with ethyl acetate (100 mL)
  4. washThe organic layer was washed with brine (10 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (1:1)

出典と根拠

ORDレコード
ord-0809d0442057451fab45fc65d8057a0a
出典データセット
uspto-grants-2011_03
特許番号
US07906532B2

反応ノート

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