Cyclopropylamine → (S)-2-Cyclopropylcarbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1185433ノート

反応式

HRID 1185433 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=C[C:19]2N(O)N=[N:22][C:20]=2[CH:21]=1.C1(N)CC1.CCN(C(C)C)C(C)C>CN(C=O)C.C(=O)([O-])O.[Na+].C(Cl)CCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13](=[O:15])[NH:22][CH:20]1[CH2:21][CH2:19]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

8

反応物 4

HCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

生成物 1

HCID 68599173(S)-2-Cyclopropylcarbamoyl-pyrrolidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 6228Dimethylformamide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of 10 g of (S)-Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester in 953 ml of DMF, 9.2 g of HOBT, 11.5 g of EDC, 3.4 g of cyclopropylamine and 13.8 g of DIPEA was added and the reaction mixture was stirred for 16 h at RT. Then, the reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic phase was washed with saturated aqueous sodium hydrogen carbonate solution and water and dried over MgSO4. The solvents were removed under reduced pressure and the crude product was pure enough for the next reaction step.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with saturated aqueous sodium hydrogen carbonate solution and water
  3. dry with materialdried over MgSO4
  4. customThe solvents were removed under reduced pressure
  5. customthe crude product was pure enough for the next reaction step

出典と根拠

ORDレコード
ord-744cd156121944e1a2f52b3d77f88894
出典データセット
uspto-grants-2014_03
特許番号
US08669266B2

反応ノート

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