Sodium Bicarbonate → Boc-hyp-obzl

HRID 2229589Notes

Reaction equation

HRID 2229589 reaction equation
[C:1]([O:5][C:6]([O:8]C([O-])=O)=O)([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[NH:17]1[CH2:32][C@H:30]([OH:31])[CH2:29][C@H:18]1[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>C1COCC1.C(OCC)(=O)C>[N:17]1([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:8])[CH2:32][C@H:30]([OH:31])[CH2:29][C@H:18]1[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 6993393benzyl (2S,4R)-4-hydroxypyrrolidine-2-carboxylateHCID 22064466Tert-butyldicarbonate

Product 1

HCID 11902907Boc-hyp-obzlYield 73.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

t-Butyldicarbonate (1.1 g) and then sat. sodium bicarbonate (20 ml) were added to a suspension of trans-Hyp-OBn (1.1 g) in THF (25 ml) and the mixture stirred for 30 min. The mixture was diluted with ethyl acetate and washed with water, dried (MgSO4) and evaporated. Flash chromatography (SiO2 DCM then ether) gave Boc-Hyp-OBn 1.18 g.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-3d9ece7082324029926ba4c5a934059a
Source dataset
uspto-grants-2002_07
Patent number
US06420438B1

Reaction notes

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