Lithium borohydride → [(S)-1-(2-Hydroxy-1-pyridin-2-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester

HRID 1040461Notes

Reaction equation

HRID 1040461 reaction equation
C[O:2][C:3](=O)[CH:4]([NH:11][C:12](=[O:23])[C@@H:13]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH3:14])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[Li+].[BH4-]>C1COCC1>[C:19]([O:18][C:16](=[O:17])[NH:15][C@H:13]([C:12](=[O:23])[NH:11][CH:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1)[CH2:3][OH:2])[CH3:14])([CH3:20])([CH3:21])[CH3:22]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 67390971HCID 67390971, compound

Product 1

HCID 67389928[(S)-1-(2-Hydroxy-1-pyridin-2-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of ((S)-2-tert-Butoxycarbonylamino-propionylamino)-pyridin-2-yl-acetic acid methyl ester (1.12 g, 3.32 mmol) in 15 mL of THF was added LiBH4 (2 M in THF, 1.66 mL, 3.32 mmol) drop wise and the reaction was stirred at room temperature for 16 h. The reaction was carefully quenched by water, neutralized with 0.1 N HCl aq., extracted with EtOAc, washed with aq. NaHCO3 and Brine. Dried over Na2SO4, filtered and concentrated in vacuo to afford [(S)-1-(2-Hydroxy-1-pyridin-2-yl-ethylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester (770 mg, 77%) as a white foam, m/z 310.60 [M+1]+

Workup

  1. customThe reaction was carefully quenched by water
  2. extractionextracted with EtOAc
  3. washwashed with aq. NaHCO3 and Brine
  4. dry with materialDried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68f4059682a540188aca634e6e09ed4f
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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