Sodium borohydride → 2-Hydroxy-3-[2-(2-methoxy-phenyl)-ethyl]-4-oxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl Ester

HRID 987085ノート

反応式

HRID 987085 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH:16]2[CH2:17][CH2:18][CH2:19][CH:12]1[C:13](=[O:31])[N:14]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30])[C:15]2=[O:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][C:9]([N:11]1[CH:12]2[CH2:19][CH2:18][CH2:17][CH:16]1[CH:15]([OH:20])[N:14]([CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH3:30])[C:13]2=[O:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 572806073-[2-(2-Methoxyphenyl)-ethyl]-2,4-dioxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl Ester2 回

生成物 1

HCID 536973812-Hydroxy-3-[2-(2-methoxy-phenyl)-ethyl]-4-oxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic Acid Benzyl Ester収率 84.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

3-[2-(2-Methoxy-phenyl)-ethyl]-2,4-dioxo-3,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound 8, 0.77g, 1.82 mmol) was dissolved in methanol (18 mL). The mixture was cooled to 0° C., and NaBH4 (0.14 g, 3.64 mmol) was added in portions from the top. The reaction was stirred for 10 minutes and then carefully quenched with water. MeOH was removed under reduced pressure, and the residue was extracted with EtOAc. The combined organic layers were washed with 10% citric acid (5 mL), water (5 mL), saturated NaHCO3 (5 mL), and brine (5 mL), and finally passed over a short plug of Na2SO4. The solvents were evaporated to give Compound 9 (0.65 g, 83%, mixture of isomers) as a clear oil, which was of sufficiently good quality to be advanced to the next step without further purification. Rf=0.5 (50% EtOAc/hexanes).

後処理

  1. customcarefully quenched with water
  2. customMeOH was removed under reduced pressure
  3. extractionthe residue was extracted with EtOAc
  4. washThe combined organic layers were washed with 10% citric acid (5 mL), water (5 mL), saturated NaHCO3 (5 mL), and brine (5 mL)
  5. customThe solvents were evaporated

出典と根拠

ORDレコード
ord-f4c5eb2bbafa452eb794fc12161be196
出典データセット
uspto-grants-2003_10
特許番号
US06630472B1

反応ノート

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