Sodium cyanoborohydride → (S)-1-(Tetrahydro-pyran-4-ylmethyl)-azepane-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

HRID 336218ノート

反応式

HRID 336218 の反応式
C([BH3-])#N.[Na+].[O:5]1[CH2:10][CH2:9][CH:8]([CH:11]=O)[CH2:7][CH2:6]1.Cl.[C:14]([C:18]1[O:22][N:21]=[C:20]([NH:23][C:24]([C@@H:26]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][NH:27]2)=[O:25])[CH:19]=1)([CH3:17])([CH3:16])[CH3:15]>CN(C=O)C.CCOC(C)=O>[C:14]([C:18]1[O:22][N:21]=[C:20]([NH:23][C:24]([C@@H:26]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][N:27]2[CH2:11][CH:8]2[CH2:7][CH2:6][O:5][CH2:10][CH2:9]2)=[O:25])[CH:19]=1)([CH3:17])([CH3:15])[CH3:16]

参加物

6

反応物 3

HCID 5003444Sodium cyanoborohydrideHCID 9964078Tetrahydro-2H-pyran-4-carboxaldehydeHCID 86660403(S)-Perhydro-azepine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide hydrochloride

生成物 1

HCID 58563913(S)-1-(Tetrahydro-pyran-4-ylmethyl)-azepane-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Sodium cyanoborohydride (0.19 g, 3.02 mmol) and tetrahydro-pyran-4-carbaldehyde (0.26 g, 2.26 mmol) is added to a solution of (S)-perhydro-azepine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide hydrochloride (prepared according to Method T, step 6) (0.4 g, 1.51 mmol) in DMF (5.0 mL). After stirring for four hours, the reaction mixture is diluted with EtOAc and washed twice with water. The organic phase is dried over anhydrous Na2SO4 and after removal of the solvent under reduced pressure, the crude is purified by prep TLC to afford the title compound; m/z 364 [M+H].

後処理

  1. washwashed twice with water
  2. dry with materialThe organic phase is dried over anhydrous Na2SO4
  3. customafter removal of the solvent under reduced pressure
  4. customthe crude is purified by prep TLC

出典と根拠

ORDレコード
ord-e9cb4a17530d4635900ad0729b303dbb
出典データセット
uspto-grants-2014_11
特許番号
US08889670B2

反応ノート

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