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

HRID 602467노트

반응식

HRID 602467 반응식
[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]

참가 물질

5

반응물 3

HCID 433294Lithium Chloride2회HCID 4311764Sodium borohydride2회HCID 866241491-tert-Butyl 2-methyl (2S,4S)-4-{[(1-isopropyl-1H-indazol-3-yl)carbonyl]amino}pyrrolidine-1,2-dicarboxylate

생성물 1

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

시약·촉매·용매 1

HCID 7360Tetrahydrofurfuryl alcohol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-0809d0442057451fab45fc65d8057a0a
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906532B2

반응 노트

불러오는 중…