Aluminium lithium hydride → HCID 57750341, 화합물

HRID 423061노트

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HRID 423061 반응식
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([O:11][C:12]([NH:14][C:15]1([C:30]([NH:32][C@@H:33]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=2)[CH2:34][C:35](OC)=[O:36])=[O:31])[CH2:20][CH2:19][N:18]([C:21]2[C:22]3[CH:29]=[CH:28][NH:27][C:23]=3[N:24]=[CH:25][N:26]=2)[CH2:17][CH2:16]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>C1COCC1>[Cl:45][C:42]1[CH:41]=[CH:40][C:39]([C@H:33]([NH:32][C:30]([C:15]2([NH:14][C:12](=[O:13])[O:11][C:7]([CH3:9])([CH3:8])[CH3:10])[CH2:16][CH2:17][N:18]([C:21]3[C:22]4[CH:29]=[CH:28][NH:27][C:23]=4[N:24]=[CH:25][N:26]=3)[CH2:19][CH2:20]2)=[O:31])[CH2:34][CH2:35][OH:36])=[CH:44][CH:43]=1

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 57750401HCID 57750401, 화합물2회

생성물 1

HCID 57750341HCID 57750341, 화합물수율 21.63%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

LiAlH4 (1.398 mL, 1.40 mmol) was added dropwise to (R)-methyl 3-(4-(tert-butoxycarbonylamino)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamido)-3-(4-chlorophenyl)propanoate (Intermediate 41) (779 mg, 1.40 mmol) in THF (40 mL) cooled to 0° C. under nitrogen. The resulting solution was stirred at 20° C. for 3 hours. The reaction mixture was quenched with water (1 mL) and neutralised with 2M HCl. The reaction mixture was evaporated to dryness and redissolved in DCM (100 mL) and washed with water (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. The pure fractions were combined and evaporated to give (R)-tert-butyl 4-(1-(4-chlorophenyl)-3-hydroxypropylcarbamoyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-ylcarbamate (160 mg, 21.63%) as a solid.

후처리

  1. customThe reaction mixture was quenched with water (1 mL)
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionredissolved in DCM (100 mL)
  4. washwashed with water (100 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto afford crude product
  9. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM
  10. customevaporated

출처 및 근거

ORD 기록
ord-2591d3d7ef94450fbba8355ffe4f789f
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101623B2

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