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

HRID 47726

Reaction equation

HRID 47726 reaction equation
[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

Participants

6

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ec9f311ab5cb4c12aab3f5e02e5e95bc
Source dataset
uspto-grants-2004_03
Patent number
US06699895B2

Linked notes

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