tert-butyl 3(S)-[N-benzyl-N-(alpha(S)-methylbenzyl)amino]-2(S)-hydroxyheptanoate → tert-butyl 3(S)-amino-2(S)-hydroxyheptanoate

HRID 635636Notes

Reaction equation

HRID 635636 reaction equation
C([N:8]([C@@H:17]([CH2:27][CH2:28][CH2:29][CH3:30])[C@H:18]([OH:26])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H](C)C1C=CC=CC=1)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[NH2:8][C@@H:17]([CH2:27][CH2:28][CH2:29][CH3:30])[C@H:18]([OH:26])[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20]

Participants

4

Reactant 1

HCID 70091290tert-butyl 3(S)-[N-benzyl-N-(alpha(S)-methylbenzyl)amino]-2(S)-hydroxyheptanoate

Product 1

HCID 20639995tert-butyl 3(S)-amino-2(S)-hydroxyheptanoateYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 0.5 g of tert-butyl 3(S)-[N-benzyl-N-(α(S)-methylbenzyl)amino]-2(S)-hydroxyheptanoate in acetic acid containing 0.2 g of palladium-on-charcoal was hydrogenolyzed overnight at 0.5 MPa. The catalyst was removed by filtration and the acetic acid was evaporated. The crude product was dissolved in dichloromethane and washed with saturated sodium bicarbonate solution. The aqueous phase was extracted with dichloromethane and the combined organic layers were washed with saturated sodium bicarbonate solution, dried over magnesium sulphate and evaporated to give 0.26 g of tert-butyl 3(S)-amino-2(S)-hydroxyheptanoate, MS: m/e 218.3 [M+H]+.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe acetic acid was evaporated
  3. dissolutionThe crude product was dissolved in dichloromethane
  4. washwashed with saturated sodium bicarbonate solution
  5. extractionThe aqueous phase was extracted with dichloromethane
  6. washthe combined organic layers were washed with saturated sodium bicarbonate solution
  7. dry with materialdried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-13f54558ed03462ba1321d7b988fb05d
Source dataset
uspto-grants-2001_02
Patent number
US06187905B1

Reaction notes

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