Acetaldehyde → HCID 86670461, compound

HRID 1777281Notes

Reaction equation

HRID 1777281 reaction equation
[CH:1](=O)[CH3:2].[C:4]([O:8][C:9]([NH:11][CH2:12][C@H:13]([NH:18][CH2:19][CH3:20])[C:14]([O:16][CH3:17])=[O:15])=[O:10])([CH3:7])([CH3:6])[CH3:5].C([BH3-])#N.[Na+].O>O1CCCC1>[C:4]([O:8][C:9]([NH:11][CH2:12][C@H:13]([N:18]([CH2:1][CH3:2])[CH2:19][CH3:20])[C:14]([O:16][CH3:17])=[O:15])=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 177AcetaldehydeHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 86670460HCID 86670460, compound

Product 1

HCID 86670461HCID 86670461, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

150 μl (2.4 mmol) of acetaldehyde are added to 369 mg (1.5 mmol) of methyl (S)-3-tert-butoxycarbonylamino-2-ethylaminopropanoate in 5 ml of tetrahydrofuran then stirred for 30 minutes at ambient temperature. After cooling to 0° C., 189 mg (3 mmol) of sodium cyanoborohydride are added and the reaction medium is stirred at ambient temperature for 36 h. Water is added and the medium is extracted with ethyl acetate. The organic phase is washed with water, dried over magnesium sulphate, filtered then concentrated. The crude residue obtained is purified by chromatography over silica gel eluted with a 70/30 heptane/ethyl acetate mixture. 150 mg (38%) of methyl (S)-3-tert-butoxycarbonylamino-2-diethylaminopropanoate are obtained in the form of a colourless oil.

Workup

  1. temperatureAfter cooling to 0° C.
  2. stirringthe reaction medium is stirred at ambient temperature for 36 h
  3. extractionthe medium is extracted with ethyl acetate
  4. washThe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationthen concentrated
  8. customThe crude residue obtained
  9. customis purified by chromatography over silica gel
  10. washeluted with a 70/30 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-c5c95652c89d441b8124b081b2c335fe
Source dataset
uspto-grants-2016_02
Patent number
US09266848B2

Reaction notes

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