n-Boc-4-(2-cyclopropyl-4-hydroxymethyl-2h-pyrazol-3-yl)-piperidine → N-Boc-4-(2-cyclopropyl-4-formyl-2H-pyrazol-3-yl)-piperidine

HRID 1350778노트

반응식

HRID 1350778 반응식
[C:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([CH:21]3[CH2:23][CH2:22]3)[N:16]=[CH:17][C:18]=2[CH2:19][OH:20])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>C1COCC1.O=[Mn]=O>[C:1]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[N:15]([CH:21]3[CH2:23][CH2:22]3)[N:16]=[CH:17][C:18]=2[CH:19]=[O:20])[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

참가 물질

4

반응물 1

HCID 21097374n-Boc-4-(2-cyclopropyl-4-hydroxymethyl-2h-pyrazol-3-yl)-piperidine

생성물 1

HCID 21097373N-Boc-4-(2-cyclopropyl-4-formyl-2H-pyrazol-3-yl)-piperidine수율 70.7%

시약·촉매·용매 2

HCID 14801Manganese dioxide촉매HCID 8028Tetrahydrofuran용매

실험 절차

The above acid (300 mg, 0.894 mmol) was dissolved in 5 mL of THF. To this solution was added 3.58 mL (3.58 mmol) of 1M borane in THF. After stirring for 5 h, the mixture was poured into 15 mL of 5% HCl. The solution was extracted with 200 mL of EtOAc, and the extract was washed with saturated NaHCO3 and brine, dried over MgSO4, filtered, concentrated, and chromatographed (10–100 EtOAc in hexanes) to give 120 mg of N-Boc-4-(2-cyclopropyl-4-hydroxymethyl-2H-pyrazol-3-yl)-piperidine. This alcohol (100 mg, 0.31 mmol) was stirred overnight in 10 mL of THF with 270 mg (3.1 mmol) of activated MnO2. The mixture was filtered and concentrated to provide 70 mg of N-Boc-4-(2-cyclopropyl-4-formyl-2H-pyrazol-3-yl)-piperidine.

후처리

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a98884386ee8443f9d944dec4fafc305
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07214802B2

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