Benzaldehyde → Methyl 2-(benzylamino)-2-phenylacetate

HRID 1951574

反応式

HRID 1951574 の反応式
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:11]([O:13][CH3:14])=[O:12].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl>[CH2:1]([NH:9][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 240BenzaldehydeHCID 117324Methyl phenylglycineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 3699844Methyl 2-(benzylamino)-2-phenylacetate

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

to a mixture of benzaldehyde (3.06 ml, 30.3 mmol) and methyl 2-amino-2-phenylacetate 1a (4.552 g, 27.6 mmol) in 50 mL 1,2-dichloroethane was added sodium triacetoxyborohydride (14.6 g, 68.9 mmol) all at once. The reaction mixture was stirred at room temperature for several hours then poured into 100 mL saturated aqueous sodium bicarbonate solution. The biphase was vigorously stirred for 15 minutes then the organic separation dried over magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to afford a colorless oil. The product was purified by chromatography on silica gel eluting with 10-40% ethyl acetate in hexane. ESI+ m/z=256.1 [MH]+.

後処理

  1. stirringThe biphase was vigorously stirred for 15 minutes
  2. customthe organic separation
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customto afford a colorless oil
  7. customThe product was purified by chromatography on silica gel eluting with 10-40% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-faf6b9ad5d1e4cbd97e017ffbeac859c
出典データセット
uspto-grants-2013_03
特許番号
US08404722B2

関連ノート

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