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3-Methylbutanal → 4-[(4-Benzyloxy-phenyl)-(3-methyl-butyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1069458
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HRID 1069458 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:29](=O)[CH2:30][CH:31]([CH3:33])[CH3:32].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:20]=2)[CH2:29][CH2:30][CH:31]([CH3:33])[CH3:32])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
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참가 물질

5

반응물 3

HCID 115523-MethylbutanalHCID 5049666Sodium triacetoxyborohydrideHCID 105479494-(4-Benzyloxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 537121684-[(4-Benzyloxy-phenyl)-(3-methyl-butyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester수율 85.1%

시약·촉매·용매 1

HCID 6344Dichloromethane
용매
2회

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온도
0 °C

실험 절차

4-(4-Benzyloxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (9.51 g, 24.9 mmol) was dissolved in CH2Cl2 (150 mL) and treated with isovaleraldehyde (2.7 mL, 24.9 mmol). The reaction was stirred for 30 minutes, then cooled to 0° C., treated with NaBH(OAc)3, allowed to warm to room temperature as the ice melted, and stir overnight. The reaction was diluted with CH2Cl2 (300 mL), washed twice with saturated sodium bicarbonate solution and once with brine, dried over Na2SO4, and concentrated. The crude material was chromatographed on silica gel eluting with 4% MeOH/CH2Cl2 to give 9.59 g (85%) of the desired product.

후처리

  1. stirringstir overnight
  2. washwashed twice with saturated sodium bicarbonate solution and once with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude material was chromatographed on silica gel eluting with 4% MeOH/CH2Cl2

출처 및 근거

ORD 기록
ord-c00c318390c94f2fac380d372c08d690
출처 데이터셋
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06251918B1

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