Hydrochloric Acid → HCID 66744415, compound

HRID 1959427Notes

Reaction equation

HRID 1959427 reaction equation
[CH2:1]([NH:3][C:4]([O:6][C@H:7]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8]1)=[O:5])[CH3:2].Cl>O1CCOCC1>[CH2:1]([NH:3][C:4](=[O:5])[O:6][C@H:7]1[CH2:11][CH2:10][NH:9][CH2:8]1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68078873HCID 68078873, compound

Product 1

HCID 66744415HCID 66744415, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Crude tert-butyl (5)-3-(ethylcarbamoyloxy)pyrrolidine-1-carboxylate from step 2 was treated with hydrogen chloride (461 μL of 4 M, 1.8 mmol) in dioxane. The reaction mixture was stirred for 1.5 h at room temperature. The solvent was removed under reduced pressure to obtain (S)-pyrrolidin-3-yl ethylcarbamate (88 mg, 73%). 1H NMR (400 MHz, DMSO-d6) δ 9.56-8.98 (m, 2H), 4.38 (s, 1H), 3.29-3.05 (m, 4H), 3.03-2.94 (m, 2H), 1.95-1.75 (m, 3H), 1.29 (dd, J=13.8, 6.6 Hz, 1H), 1.01 (t, J=7.2 Hz, 1H). LC/MS m/z 159.4 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-80b23c13cc71404eb82c069533b20454
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

Loading…