1-Naphthaldehyde → (S)-1,1-diethoxy-N-(naphthalen-1-ylmethyl)propan-2-amine

HRID 1254489

反応式

HRID 1254489 の反応式
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C@@H:5]([NH2:7])[CH3:6])[CH3:2].[C:11]1([CH:21]=O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C@@H:5]([NH:7][CH2:21][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:6])[CH3:2]

参加物

6

反応物 3

HCID 61951-NaphthaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 12398111(2S)-1,1-Diethoxy-2-propanamine

生成物 1

HCID 67075196(S)-1,1-diethoxy-N-(naphthalen-1-ylmethyl)propan-2-amine収率 67.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To the solution of (S)-1,1-diethoxypropan-2-amine (Compound XIX-1) 682 mg (3.55 mmol) in tetrahydrofuran 2 ml, 1-naphthaldehyde 554 mg (3.55 mmol) was added and stirred at room temperature for 0.5 hour. The reaction mixture was diluted with tetrahydrofuran 3 ml and sodium triacetoxyborohydride 829 mg (3.91 mmol) was added and stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate 50 ml and washed with saturated sodium bicarbonate aq. 50 ml twice, water 50 ml twice and brine 50 ml twice. The organic phase was dried with magnesium sulfate and filtered and the mother solution was concentrated in vacuo to obtain the title compound 685 mg (67.1%).

後処理

  1. additionwas added
  2. stirringstirred at room temperature for 18 hours
  3. washwashed with saturated sodium bicarbonate aq. 50 ml twice
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe mother solution was concentrated in vacuo

出典と根拠

ORDレコード
ord-a4667eb89f334e58b4fe84db0cc95cb3
出典データセット
uspto-grants-2013_06
特許番号
US08455488B2

関連ノート

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