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

HRID 877691ノート

反応式

HRID 877691 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-42293847ad9d418fa9947706eb010bd3
出典データセット
uspto-grants-2015_03
特許番号
US08987268B2

反応ノート

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