Acetaldehyde → (R)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate

HRID 1476317ノート

反応式

HRID 1476317 の反応式
[NH2:1][CH2:2][C@@H:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[CH:16](=O)[CH3:17].[C:19](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:20].[Na+]>C(Cl)Cl>[CH2:19]([N:1]([CH2:2][C@@H:3]1[CH2:8][O:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:16][CH3:17])[CH3:20]

参加物

5

反応物 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 44182323(R)-tert-Butyl 3-(aminomethyl)morpholine-4-carboxylate

生成物 1

HCID 66723762(R)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of (R)-tert-butyl 3-(aminomethyl)morpholine-4-carboxylate (commercially available, 250 mg, 1.16 mmol) and DCM (7 ml) at 0° C. was treated with acetaldehyde (0.162 ml, 2.89 mmol). The reaction mixture was stirred at 0° C. for 15 minutes and sodium triacetoxyborohydride (612 mg, 2.89 mmol) was added all at once. The resulting mixture was stirred for 24 h and the mixture was diluted with 20 ml of DCM (20 ml) and washed with saturated aq. sodium bicarbonate (20 ml). The organic phase was dried over sodium sulfate, filtered, and concentrate under pressure to give (R)-tert-butyl 3-((diethylamino)methyl)morpholine-4-carboxylate (INTERMEDIATE 90, STEP 1)

後処理

  1. stirringThe resulting mixture was stirred for 24 h
  2. washwashed with saturated aq. sodium bicarbonate (20 ml)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrate under pressure

出典と根拠

ORDレコード
ord-125bc16c39aa4681a34f44f25a0295bc
出典データセット
uspto-grants-2015_04
特許番号
US09018381B2

反応ノート

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