rac-(3R,4S)-4-aminooxolan-3-ol → trans-(+/-)-4-[(3,6-Diethylpyrazin-2-yl)amino]tetrahydrofuran-3-ol

HRID 1612300Notes

Reaction equation

HRID 1612300 reaction equation
[CH2:1]([C:3]1[C:4]([NH:11][C@H:12]2[C@@H:16]([OH:17])[CH2:15]N(C(OCC3C=CC=CC=3)=O)[CH2:13]2)=[N:5][C:6]([CH2:9][CH3:10])=[CH:7][N:8]=1)[CH3:2].N[C@@H]1C[O:32]C[C@H]1O>>[CH2:1]([C:3]1[C:4]([NH:11][C@@H:12]2[CH2:13][O:32][CH2:15][C@H:16]2[OH:17])=[N:5][C:6]([CH2:9][CH3:10])=[CH:7][N:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 11768516rac-(3R,4S)-4-aminooxolan-3-olHCID 60044796benzyl (3R,4S)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 86588871trans-(+/-)-4-[(3,6-Diethylpyrazin-2-yl)amino]tetrahydrofuran-3-ol

Procedure

Following the procedure for the preparation of benzyl (3R,4S)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-hydroxypyrrolidine-1-carboxylate but substituting trans-(+/−)-4-aminotetrahydrofuran-3-ol and making non-critical variations provided the title compound as an orange oil. IR (diffuse reflectance) 3356, 3255, 2972, 2938, 1587, 1511, 1464, 1453, 1396, 1337, 1185, 1099, 1064, 965, 888 cm−1; OAMS supporting ions at: ESI+ 238.1; MS (EI) m/z 237 (M+); HRMS (FAB) calcd for C12H19N3O2+H1 238.1555, found 238.1551.

Sources & evidence

ORD record
ord-56ffb084394d4f7f9fa18aaeabfae9b6
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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