Sodium Hydroxide → (2S,4R)-1-allyloxycarbonyl-2-methoxycarbonyl-4-hydroxypyrrolidine

HRID 2399264Notes

Reaction equation

HRID 2399264 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@@H:5]1[CH2:9][CH:8]([OH:10])[CH2:7][NH:6]1.Cl[C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14].[OH-].[Na+]>O.C1COCC1>[CH3:2][O:3][C:4](=[O:11])[C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 18052Allyl chloroformateHCID 12764091methyl (2S)-4-hydroxypyrrolidine-2-carboxylate hydrochloride

Product 1

HCID 10633157(2S,4R)-1-allyloxycarbonyl-2-methoxycarbonyl-4-hydroxypyrrolidineYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-hydroxyproline methyl ester hydrochloride (Rosen et al, Synthesis, 40, 1988) (60.4 mMol) in water (10 ml) and THF (20 ml), at 0° C., was added dropwise allyl chloroformate (70 mMol) in THF (20 ml). The solution was maintained at a slightly basic pH by the simultaneous addition of 4N sodium hydroxide (144 mMol). The mixture was stirred at 0° for 1 hour. The aqueous layer was separated and washed, twice, with dichloromethane (25 ml). The organic layers were combined, dried and evaporated to give N-allyloxycarbonyl hydroxyproline methyl ester as a pale yellow oil (86%): NMR (CDCl3) 2.2(m, 3H); 3.58(m, 2H); 3.73(2d, 3H); 4.54(m, 4H); 5.25(m, 2H); 5.9(m, 1H): M/S CI (M+H)+ =230.

Workup

  1. customThe aqueous layer was separated
  2. washwashed
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-59ff967cb361412e9ab65ec81b93c7cd
Source dataset
uspto-grants-1995_09
Patent number
US05447925

Reaction notes

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