Hydrochloric Acid → HCID 57463460, compound

HRID 2221008Notes

Reaction equation

HRID 2221008 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@@H:7]([CH3:8])[CH2:6][CH2:5][N:4]1C(OC(C)(C)C)=O.CO.[ClH:18]>C(Cl)Cl.O1CCOCC1>[ClH:18].[CH3:8][C@H:7]1[CH2:6][CH2:5][NH:4][C@@H:3]1[CH2:2][OH:1]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 45097414HCID 45097414, compound

Product 1

HCID 57463460HCID 57463460, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

The crude 1,1-dimethylethyl(2S,3S)-2-(hydroxymethyl)-3-methyl-1-pyrrolidinecarboxylate from step 3 was dissolved in a 1:1 mixture of methylene chloride:methanol. Excess 4N HCl in dioxane was added, and the reaction stirred at room temperature for 1 hour, concentrated under reduced pressure, and then used in the final step (see Scheme 1a (g) to (h)). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.1 (d, J=6.2 Hz, 3 H) 1.5 (m, 1 H) 2.1 (m, 2 H) 3.1 (m, 1 H) 3.3 (m, 1 H) 3.4 (m, 1 H) 4.5 (dd, J=12.1, 8.1 Hz, 1 H) 4.7 (dd, J=12.3, 3.1 Hz, 1 H).

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b6c797b3545b423a85c3d90b3435c733
Source dataset
uspto-grants-2008_05
Patent number
US07368453B2

Reaction notes

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