Water → Benzyl 2-(1-aminoethyl)morpholine-4-carboxylate

HRID 1527135ノート

反応式

HRID 1527135 の反応式
[C:1]([CH:4]1[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1)(=O)[CH3:2].C([O-])(C)=O.[NH4+].[BH3-]C#[N:27].[Na+].O>C1COCC1.CO>[NH2:27][CH:1]([CH:4]1[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1)[CH3:2]

参加物

6

反応物 4

HCID 962WaterHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 18354411Phenylmethyl 2-acetyl-4-morpholinecarboxylate

生成物 1

HCID 18354340Benzyl 2-(1-aminoethyl)morpholine-4-carboxylate収率 40%

試薬・触媒・溶媒 1

HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

To a solution of benzyl 2-acetylmorpholine-4-carboxylate (5.0 g, 19 mmol) in THF/MeOH (1/5, 100 mL) were added AcONH4 (14.6 g, 190 mmol) and NaBH3CN (11.8 g, 190 mmol). The mixture was stirred at room temperature for 50 hr. The mixture was concentrated to give the crude. Water (20 mL) was added and the mixture was extracted by ethyl acetate (60 mL*3). 1N HCl was added into the combined organic layers. The aqueous layer was concentrated, brought to above pH >8 with 2N NaOH and extracted by ethyl acetate (60 mL*3). The organic layer was washed with brine, dried over sodium sulfate. The mixture was concentrated to give benzyl 2-(1-aminoethyl)morpholine-4-carboxylate (2.0 g, 40%).

後処理

  1. concentrationThe mixture was concentrated
  2. customto give the crude
  3. extractionthe mixture was extracted by ethyl acetate (60 mL*3)
  4. addition1N HCl was added into the combined organic layers
  5. concentrationThe aqueous layer was concentrated
  6. extractionextracted by ethyl acetate (60 mL*3)
  7. washThe organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. concentrationThe mixture was concentrated

出典と根拠

ORDレコード
ord-10c0b5c22fcc4dd2a491eeaaeb51f853
出典データセット
uspto-grants-2015_07
特許番号
US09085583B2

反応ノート

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