Triethylamine → (S)-1-Amino-3-morpholinopropan-2-ol

HRID 481048Notes

Reaction equation

FC1C=C2C(=CC=1)NC(=O)C2.N1C=CN=C1C(N)=O.[NH2:20][CH2:21][C@@H:22]([OH:30])[CH2:23][N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C(N(CC)CC)C>C(#N)C.O1CCCC1>[NH2:20][CH2:21][C@H:22]([OH:30])[CH2:23][N:24]1[CH2:25][CH2:26][O:27][CH2:28][CH2:29]1

Participants

Conditions

Temperature: 60 °C

Procedure

A 0.25 L flask fitted with a thermometer, condenser, magnetic stirring, and nitrogen inlet was charged with 4.92 g 5-Fluorooxindole, 7.0 g Imidazole amide, 15.5 g (R)-1-Amino-3-(4-morpholinyl)-2-propanol, 9.78 g Triethylamine and 88 ml Tetrahydrofuran. The mixture was heated to 60° C. for 16.5 hours. The reaction is cooled to ambient temperature and filtered. The solids obtained are slurried (3) three successive times in acetonitrile at 11 ml/g, dried in vacuo for 3.6 g (25.25%). [HPLC, Hypersil BDS, C-18, 5μ, (6:4), Acetonitrile:0.1M Ammonium Chloride, PHA-571437=4.05 min.] H1NMR (DMSO): δ10.86 (1H,bs); 7.75 (1H,d); 7.70 (1H,s); 7.50 (1H,m); 6.88 (2H,m); 4.72 (1H,bs); 3.78 (1H,bs); 3.56 (4H,m); 3.32 (6H,m); 3.15 (1H,m); 2.43 (8H,bm).

Workup

customA 0.25 L flask fitted with a thermometer, condenser, magnetic stirring, and nitrogen inlet
temperatureThe reaction is cooled to ambient temperature
filtrationfiltered
customThe solids obtained
customdried in vacuo for 3.6 g (25.25%)
custom[HPLC, Hypersil BDS, C-18, 5μ, (6:4), Acetonitrile:0.1M Ammonium Chloride, PHA-571437=4.05 min.] H1NMR (DMSO): δ10.86 (1H,bs); 7.75 (1H,d); 7.70 (1H,s); 7.50 (1H,m); 6.88 (2H,m); 4.72 (1H,bs); 3.78 (1H,bs); 3.56 (4H,m); 3.32 (6H,m); 3.15 (1H,m); 2.43 (8H,bm)

Sources & evidence

ORD record: ord-820c9e8cd342407cad4af1e86170df90
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06653308B2

Reaction notes

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