Ethanolamine → (4S)-4-Isobutyl-2-isopropyloxazolidine

HRID 276691

Reaction equation

[CH3:1][O:2][C:3](=O)[C@H:4]([CH2:6][CH:7]([CH3:9])[CH3:8])[NH2:5].O[CH2:12][C@@H:13](N)[CH2:14]C(C)C.OCCN.C(=O)C(C)C>>[CH:13]([CH:1]1[NH:5][C@@H:4]([CH2:6][CH:7]([CH3:9])[CH3:8])[CH2:3][O:2]1)([CH3:14])[CH3:12]

Participants

Reactant 4

HCID 700Ethanolamine

HCID 6561Isobutyraldehyde

HCID 65105(+)-L-Leucine methyl ester

HCID 111307L-Leucinol

Product 1

HCID 45096513(4S)-4-Isobutyl-2-isopropyloxazolidine

Procedure

(L)-Leucine methyl ester was reduced to (1S)-1-(hydroxymethyl)-3-methylbutylamine according to Method B1b, Step 2. The 2-hydroxyethylamine was reacted with isobutyraldehyde according to Method B4c, Step 1 to afford (4S)-2-isopropyl-4-isobutyl-1,3-oxazolidine. The oxazolidine was reduced according to Method B4c, Step 2 to give (1S)-1-(hydroxymethyl)-N-isobutyl-3-methylbutylamine. The substituted 2-hydroxyethylamine was reacted with SOCl2 according to Method B7b to give (1S)-1-(chloromethyl)-N-isobutyl-3-methylbutylamine. The chloroethylamine was reacted with 2-methyl-4-nitrophenyl isocyanate according to Method C4a to afford (4S)-2-(2-methyl-4-nitrophenylimino)-3,4-diisobutyl-1,3-oxazolidine.

Sources & evidence

ORD record: ord-6afa352da51d451695531e54ac394c94
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Linked notes

Loading…