Aniline → N-phenyl-2(S)-(tert-butoxycarbonylamino)-3-phenylpropanamine

HRID 342627

反応式

HRID 342627 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([O:12][C:13]([NH:15][C@@H:16]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:17]=O)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:2]1([NH:1][CH2:17][C@@H:16]([NH:15][C:13]([O:12][C:8]([CH3:9])([CH3:11])[CH3:10])=[O:14])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6115AnilineHCID 5049666Sodium triacetoxyborohydrideHCID 6998013tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

生成物 1

HCID 10568153N-phenyl-2(S)-(tert-butoxycarbonylamino)-3-phenylpropanamine

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

Aniline (3.00 mL, 32.9 mmol) was dissolved in dichloroethane under nitrogen. The product from Step B was added (7.0 g, 29.91) and the reaction stirred for 1 h at room temperature. Sodium triacetoxyborohydride (9.51 g, 44.86 mmol) was added, and the pH adjusted to 5. The reaction was stirred overnight, then quenched with saturated sodium bicarbonate solution. The aqueous layer was removed, the organic phase washed with saturated brine and dried over magnesium sulfate. The title compound was obtained after chromatography on silica get with 8% ethyl acetate in hexane.

後処理

  1. stirringThe reaction was stirred overnight
  2. customquenched with saturated sodium bicarbonate solution
  3. customThe aqueous layer was removed
  4. washthe organic phase washed with saturated brine
  5. dry with materialdried over magnesium sulfate

出典と根拠

ORDレコード
ord-f57ec193bbda4bb2aa202df914e8578b
出典データセット
uspto-grants-1999_01
特許番号
US05859012

関連ノート

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