Diisopropylethylamine → L-Proline, 1,4,4-trimethyl-

HRID 1402284Notes

Reaction equation

HRID 1402284 reaction equation
Cl.[CH3:2][C:3]1([CH3:11])[CH2:7][NH:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4]1.[CH3:12]CN(C(C)C)C(C)C>[Pd].C=O>[CH3:12][N:6]1[CH2:7][C:3]([CH3:11])([CH3:2])[CH2:4][C@H:5]1[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 71742193(S)-4,4-Dimethylpyrrolidine-2-carboxylic acid hydrochloride

Product 1

HCID 86687126L-Proline, 1,4,4-trimethyl-Yield 99.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 712FormaldehydeSolvent

Procedure

A suspension of 4,4-dimethyl-L-proline hydrochloride (900 mg, 5.00 mmol), formaldehyde (37% aqueous, 450 μL), DIPEA (645 mg, 5.00 mmol) and palladium on carbon (10%, 400 mg) in IMS (50 mL) was stirred under an atmosphere of hydrogen (1 atm) for 4 h. The suspension was filtered and concentrated in vacuo to give the title compound as a viscous pink oil (780 mg, 99%). 1H NMR (400 MHz, CDCl3): 1.47 (3H, s), 1.49 (3H, s), 2.04-2.16 (1H, m), 2.23-2.34 (1H, m), 2.93 (3H, s), 3.10 (2H, m), 3.78-3.89 (1H, m), 4.86 (1H, br s).

Workup

  1. filtrationThe suspension was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4861eaf78a2d4068918a3a5f9046b8ad
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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