Benzoic Acid → (S)-3-benzoyloxy-1-t-butoxycarbonylpyrrolidine

HRID 1808733Notes

Reaction equation

HRID 1808733 reaction equation
ClCCl.[C:4]([OH:12])(=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.CN(C)CCCN=C=NCC.O[C@H:26]1[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27]1>O.C(OCC)C>[C:5]1([C:4]([O:12][C@H:30]2[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:29]2)=[O:11])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 243Benzoic AcidHCID 6344DichloromethaneHCID 854055tert-Butyl (3S)-3-hydroxypyrrolidine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 15117240(S)-3-benzoyloxy-1-t-butoxycarbonylpyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a dichloromethane (100 mL) solution of benzoic acid (4.03 g, 33.0 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (10.4 g, 54.0 mmol) was added tert-butyl (3S)-3-hydroxypyrrolidine-1-carboxylate (5.62 g, 30.0 mmol). The reaction mixture was stirred for 6 hours at room temperature, diluted with water (200 mL) and charged with diethyl ether (200 mL). The combined organic extracts were washed with saturated aqueous sodium hydrogencarbonate, brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound. This crude product was used in the subsequent step without further purification.

Workup

  1. washThe combined organic extracts were washed with saturated aqueous sodium hydrogencarbonate, brine
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5de15496ecd843bc823656f5cdf721ab
Source dataset
uspto-grants-2013_01
Patent number
US08361994B2

Reaction notes

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