Benzyl (3r,4r)-3-amino-4-hydroxypyrrolidine-1-carboxylate → Benzyl(trans)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-hydroxypyrrolidine-1-carboxylate

HRID 1824182Notes

Reaction equation

HRID 1824182 reaction equation
[CH2:1]([C:3]1[C:4]([NH:11][C@H:12]2[C@@H:16]([OH:17])[CH2:15][N:14]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:13]2)=[N:5][C:6]([CH2:9][CH3:10])=[CH:7][N:8]=1)[CH3:2].N[C@H]1[C@H](O)CN(C(OCC2C=CC=CC=2)=O)C1>>[CH2:1]([C:3]1[C:4]([NH:11][C@H:12]2[C@H:16]([OH:17])[CH2:15][N:14]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:13]2)=[N:5][C:6]([CH2:9][CH3:10])=[CH:7][N:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 58583247Benzyl (3r,4r)-3-amino-4-hydroxypyrrolidine-1-carboxylateHCID 60044796benzyl (3R,4S)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 58583250Benzyl(trans)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-hydroxypyrrolidine-1-carboxylate

Procedure

Following the procedure for the preparation of benzyl(3R,4S)-3-[(3,6-diethylpyrazin-2-yl)amino]-4-hydroxypyrrolidine-1-carboxylate but substituting benzyl(trans)-3-amino-4-hydroxypyrrolidine-1-carboxylate and making non-critical variations provided the title compound as a oil: 1H NMR (300 MHz, CDCl3) δ) 7.78, 7.39, 6.41, 6.22, 5.18, 4.51–3.95, 3.40, 2.65, 1.31–1.26; (MS/CI) calcd for C20H26N4O3+H 371.4, found 370.9.

Sources & evidence

ORD record
ord-b996cb13bf0847bd990158defaa35872
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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