Sodium borohydride → 543713-48-0

HRID 2111676ノート

反応式

HRID 2111676 の反応式
[BH4-].[Na+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[O:10][N:9]=1)=O)C>C(O)C>[OH:5][CH2:6][C:8]1[CH:12]=[C:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[O:10][N:9]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 10588096Ethyl 5-(aminomethyl)isoxazole-3-carboxylate, 5-BOC protected

生成物 1

HCID 67284568543713-48-0収率 91.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Sodium borohydride (610 mg, 16 mmol) was added in portions to a solution of 3-ethoxycarbonyl-5-[N-(tert-butyloxycarbonyl)aminomethyl]isoxazole (Method 73; 1.62 g, 6 mmol) in ethanol (15 ml) at 0° C. under a nitrogen atmosphere. The mixture was stirred at ambient temperature for 4 hours then quenched with saturated aqueous sodium hydrogen carbonate solution. The mixture was extracted with EtOAc and the organics washed with brine then dried (MgSO4). The solvent was removed by evaporation to give the title compound (1.25 g, 91%). NMR (DMSO): 1.38 (s, 9H), 4.21 (d, 2H), 4.44 (s, 2H), 5.40 (br s, 1H), 6.21 (s, 1H), 7.49 (br s, 1H); m/z 229 (MH)+.

後処理

  1. customthen quenched with saturated aqueous sodium hydrogen carbonate solution
  2. extractionThe mixture was extracted with EtOAc
  3. washthe organics washed with brine
  4. dry with materialthen dried (MgSO4)
  5. customThe solvent was removed by evaporation

出典と根拠

ORDレコード
ord-07fe8723aa004bea94974bd30ed18511
出典データセット
uspto-grants-2009_04
特許番号
US07521453B2

反応ノート

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