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Isovanillin → 1-(3-hydroxy-4-methoxybenzyl)-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine

HRID 279315
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인쇄 미리보기

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HRID 279315 반응식
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([CH:20]=[CH:21][CH:22]=1)[C:6]([NH:8][CH2:9][C:10]([NH:12][CH2:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)=[O:11])=[O:7].[OH:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH:29]=O.[BH3-]C#N.[Na+]>CC(O)=O.CO>[OH:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[CH2:29][N:17]1[CH2:18][CH2:19][CH:14]([CH2:13][NH:12][C:10](=[O:11])[CH2:9][NH:8][C:6](=[O:7])[C:5]2[CH:20]=[CH:21][CH:22]=[C:3]([C:2]([F:1])([F:23])[F:24])[CH:4]=2)[CH2:15][CH2:16]1
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참가 물질

5

반응물 3

HCID 12127IsovanillinHCID 5003444Sodium cyanoborohydrideHCID 184261644-[{N-(3(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine

생성물 1

HCID 184262631-(3-hydroxy-4-methoxybenzyl)-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine

시약·촉매·용매 1

HCID 10129899Acetic acid methanol용매2회

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온도
60 °C

실험 절차

To a solution of 4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (20.0 mg, 0.058 mmol) and 3-hydroxy-4-methoxybenzaldehyde (33 mg) in 5% CH3COOH/CH3OH (1.0 mL) was added NaBH3CN (16.5 mg) in 5% CH3COOH/CH3OH (1.0 mL). The reaction mixture was stirred at 60° C. for 15 h. The reaction mixture was loaded onto Variant™ SCX column and washed with CH3OH (15 mL). Product was eluted using 2 N NH3-CH3OH (5 mL) and the eluant was concentrated to afford 1-(3-hydroxy-4-methoxybenzyl)-4-[{N-(3-(trifluoromethyl)benzoyl)glycyl}aminomethyl]piperidine (Compound No. 1452) (25.8 mg, 92%): The purity was determined by RPLC/MS (91%); ESI/MSm/e 480 (M++H, C24H28F3N3O4).

후처리

  1. washwashed with CH3OH (15 mL)
  2. washProduct was eluted
  3. concentrationthe eluant was concentrated

출처 및 근거

ORD 기록
ord-b8c0f279c7874b01be9da2e7eafd4e35
출처 데이터셋
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06362177B1

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