Sodium Bicarbonate → (R)-3-N-Cbz-aminopyrrolidine

HRID 1696973Notes

Reaction equation

HRID 1696973 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:17])[NH:11][C@@H:12]1[CH2:16][CH2:15][NH:14][CH2:13]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:2]([O:9][C:10](=[O:17])[NH:11][C@@H:12]1[CH2:16][CH2:15][NH:14][CH2:13]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 45072663(R)-Benzyl pyrrolidin-3-ylcarbamate hydrochloride

Product 1

HCID 40425229(R)-3-N-Cbz-aminopyrrolidineYield 64.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-pyrrolidin-3-yl-carbamic acid benzyl ester hydrochloride (0.88 g, 3.45 mmol) in DCM is free-based using sodium hydrogen carbonate solution to yield (R)-pyrrolidin-3-yl-carbamic acid benzyl ester (0.487 g, 2.22 mmol). This amine is added to N-{(1S,2R,3S,4R)-4-[2-chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,3-dihydroxy-cyclopentyl}-propionamide (Example 4) (0.5 g, 0.96 mmol) and TEA (0.224 g, 2.22 mmol) and then dissolved in NMP (7 ml). The reaction mixture is heated using microwave radiation in a Personal Chemistry Emrys™ Optimizer microwave reactor at 190° C. for 1 hour. The resulting mixture is purified by chromatography on silica eluting with 5% MeOH in DCM to yield the titled compound.

Sources & evidence

ORD record
ord-06459fd20947455eaa5ec20c6d7c1883
Source dataset
uspto-grants-2012_04
Patent number
US08163754B2

Reaction notes

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