Sodium borohydride → N-[(1R)-2-hydroxy-1-(3-cyanobenzyl)ethyl]acetamide

HRID 1280625

反応式

HRID 1280625 の反応式
[C:1]([NH:4][C@H:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=1)[C:6](OCC)=[O:7])(=[O:3])[CH3:2].[BH4-].[Na+]>C(O)C.O.C(OCC)(=O)C>[OH:7][CH2:6][C@H:5]([NH:4][C:1](=[O:3])[CH3:2])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=1

参加物

6

反応物 2

HCID 4311764Sodium borohydrideHCID 86584426ethyl (2R)-2-acetylamino-3-(3-cyanophenyl)propanoate

生成物 1

HCID 69698344N-[(1R)-2-hydroxy-1-(3-cyanobenzyl)ethyl]acetamide収率 77%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
20 °C

実験手順

The process is performed as in Example 2, starting with 3.3 g of ethyl (2R)-2-acetylamino-3-(3-cyanophenyl)propanoate and 1.23 g of sodium borohydride in 50 cm3 of ethanol and working at a temperature in the region of −30° C. After stirring for 16 hours at a temperature in the region of 20° C., the reaction medium is evaporated under reduced pressure (5 kPa) at a temperature in the region of 45° C. and the residue obtained is then stirred in a mixture of 100 cm3 of water and 100 cm3 of ethyl acetate. The organic phase is separated out after settling has taken place and the aqueous phase is extracted with twice 100 cm3 of ethyl acetate. The organic extracts are combined and then washed with twice 50 cm3 of water, dried over magnesium sulfate, filtered and evaporated under reduced pressure (5 kPa) at a temperature in the region of 45° C. 2.13 g of N-[(1R)-2-hydroxy-1-(3-cyanobenzyl)ethyl]acetamide are obtained in the form of a white solid. (αD20=+7.5±0.6 at a concentration of 0.5% in methanol).

後処理

  1. customworking at a temperature in the region of −30° C
  2. customthe reaction medium is evaporated under reduced pressure (5 kPa) at a temperature in the region of 45° C.
  3. customthe residue obtained
  4. customThe organic phase is separated out after settling
  5. extractionthe aqueous phase is extracted with twice 100 cm3 of ethyl acetate
  6. washwashed with twice 50 cm3 of water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure (5 kPa) at a temperature in the region of 45° C

出典と根拠

ORDレコード
ord-152b58696727415e98e60c06f4af4c7b
出典データセット
uspto-grants-2002_09
特許番号
US06451821B1

関連ノート

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