p-Toluenesulfonic acid → 3-((S)-1-cyclopentyloxycarbonyl-3-methyl-butylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 632560노트

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HRID 632560 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC1C=CC(S(O)(=O)=O)=CC=1.[CH:26]1([O:31][C:32](=[O:39])[C@@H:33]([NH2:38])[CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:30][CH2:29][CH2:28][CH2:27]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClC(Cl)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:38][C@H:33]([C:32]([O:31][CH:26]2[CH2:27][CH2:28][CH2:29][CH2:30]2)=[O:39])[CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 5

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 2756825Tert-butyl 3-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 53718217(S)-cyclopentyl 2-amino-4-methylpentanoate

생성물 1

HCID 866864133-((S)-1-cyclopentyloxycarbonyl-3-methyl-butylamino)-piperidine-1-carboxylic acid tert-butyl ester수율 95.5%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of 3-oxo-piperidine-1-carboxylic acid tert-butyl ester (0.458 g, 2.3 mmol) in dichloroethane (18 mL) was added the tosic acid salt of (S)-2-amino-4-methyl-pentanoic acid cyclopentyl ester (0.496 g, 2.53 mmol) and sodium triacetoxyborohydride (0.975 g, 4.6 mmol). The solution was stirred at room temperature for 18 hours. An aqueous solution of sodium hydrogen carbonate (20 mL) was added and the mixture stirred for 20 minutes. The desired product was extracted into ethyl acetate (3 times 15 mL). The organic layers were combined, dried (MgSO4) and concentrated to give the desired product (0.840 g, 95% yield) which was used without further purification. LC/MS: m/z 383 [M+H]+

후처리

  1. stirringthe mixture stirred for 20 minutes
  2. extractionThe desired product was extracted into ethyl acetate (3 times 15 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-01662dbdddfd4c719d0e62da3d54fcf8
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321718B2

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