Benzylamine → tert-butyl 5-(benzylamino)-4-methylhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

HRID 877691노트

반응식

HRID 877691 반응식
[CH3:1][CH:2]1[CH:9]2[CH:5]([CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8]2)[CH2:4][C:3]1=O.[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.S([O-])([O-])(=O)=O.[Mg+2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:18]([NH:25][CH:3]1[CH2:4][CH:5]2[CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH:9]2[CH:2]1[CH3:1])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

6

반응물 4

HCID 7504BenzylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5049666Sodium triacetoxyborohydrideHCID 68291201tert-butyl 4-methyl-5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

생성물 1

HCID 68290857tert-butyl 5-(benzylamino)-4-methylhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

A solution of tert-butyl 4-methyl-5-oxohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (10.7 g, 44.7 mmol) and benzyl amine (7.67 g, 71.5 mmol) in 1,2-dichloroethane (250 mL) was stirred at room temperature for 2 h. Anhydrous magnesium sulfate (20 g, 166 mmol) was added. The resultant suspension was stirred at room temperature for additional 2 h. Sodium triacetoxyborohydride (18.95 g, 89 mmol) was added. After 60 h at room temperature, the mixture was quenched with saturated sodium bicarbonate (100 mL) and extracted with ethyl acetate (3×150 mL). The combined organic extracts were washed with water, brine, dried (MgSO4) and concentrated. Silica gel chromatography, eluting with 0-8% methanol in dichloromethane, gave tert-butyl 5-(benzylamino)-4-methylhexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate as a mixture of stereoisomers (13.2 g), which was taken to the next reaction without separation.

후처리

  1. customthe mixture was quenched with saturated sodium bicarbonate (100 mL)
  2. extractionextracted with ethyl acetate (3×150 mL)
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washSilica gel chromatography, eluting with 0-8% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-42293847ad9d418fa9947706eb010bd3
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987268B2

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