Sodium hydride → tert-Butyl 4-((2-methoxy-5-(2-methyl-2H-tetrazol-5-yl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate

HRID 391406노트

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HRID 391406 반응식
Br[CH2:2][C:3]1[CH:4]=[C:5]([C:11]2[N:12]=[N:13][N:14]([CH3:16])[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[OH:17][CH2:18][C:19]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]1.[H-].[Na+]>CN(C)C=O>[CH3:10][O:9][C:8]1[CH:7]=[CH:6][C:5]([C:11]2[N:12]=[N:13][N:14]([CH3:16])[N:15]=2)=[CH:4][C:3]=1[CH2:2][O:17][CH2:18][C:19]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH2:21][CH2:20]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 9994433Tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylateHCID 589936045-(3-(Bromomethyl)-4-methoxyphenyl)-2-methyl-2H-tetrazole

생성물 1

HCID 58993454tert-Butyl 4-((2-methoxy-5-(2-methyl-2H-tetrazol-5-yl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

5-(3-(Bromomethyl)-4-methoxyphenyl)-2-methyl-2H-tetrazole (35.0 mg, 0.12 mmol) and tert-butyl 4-(hydroxymethyl)-4-phenylpiperidine-1-carboxylate (40.0 mg, 0.14 mmol) were combined in dimethylformamide (1 mL) and cooled to 0° C. The reaction was treated with sodium hydride (3.2 mg, 0.14 mmol), stirred at 0° C. for 1 h, and at room temperature overnight. The solvents were removed in vacuo and the crude product purified by column chromatography on silica gel (30% ethyl acetate/hexanes) to afford 30 mg (50%). LC/MS (HPLC method 3): tR=3.29 min, 494.25 (MH)+.

후처리

  1. customat room temperature
  2. customovernight
  3. customThe solvents were removed in vacuo
  4. customthe crude product purified by column chromatography on silica gel (30% ethyl acetate/hexanes)
  5. customto afford 30 mg (50%)

출처 및 근거

ORD 기록
ord-6500b65be31b47969eedd3e7a9eb5c6c
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383821B2

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