Pyridine → (R)-3-tert-Butoxycarbonylamino-pyrrolidine-1-carboxylic acid phenyl ester

HRID 215873Notes

Reaction equation

Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].N1C=CC=CC=1.[C:17]([O:21][C:22](=[O:29])[NH:23][C@@H:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl>[C:5]1([O:4][C:2]([N:26]2[CH2:27][CH2:28][C@@H:24]([NH:23][C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:29])[CH2:25]2)=[O:3])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Phenyl chloroformate (1 eq.) is added dropwise to a solution of pyridine in DCM. The reaction mixture is cooled to 0° C. and a solution of (R)-pyrrolidin-3-yl-carbamic acid tert-butyl ester (1 eq.) in DCM is added dropwise. The reaction mixture is stirred at RT for 1 hour. The reaction mixture is partitioned between (0.2 M) HCl)(aq) and DCM. The organics are washed with water, (sat)NaHCO3(aq) and brine. The organics are dried (MgSO4), filtered and reduced in vacuo to yield the title compound.

Workup

customThe reaction mixture is partitioned between (0.2 M) HCl)(aq) and DCM
washThe organics are washed with water, (sat)NaHCO3(aq) and brine
dry with materialThe organics are dried (MgSO4)
filtrationfiltered

Sources & evidence

ORD record: ord-993da7804b3a4e1887dccdba46c33c71
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193164B2

Reaction notes

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