Benzyl Bromide → Rel-n-(2-{[(3r,4r)-4-(allyloxy)-1-(tetrahydro-2h-pyran-4-yl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide

HRID 564412Notes

Reaction equation

HRID 564412 reaction equation
[CH2:1]([O:8][C@@H:9]1[CH2:13][N:12]([CH:14]2[CH2:19]CN(C3C=NC(OC)=CC=3)C[CH2:15]2)[CH2:11][C@H:10]1[NH:28][C:29](=[O:44])[CH2:30][NH:31][C:32](=[O:43])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=1)[C:2]1C=CC=C[CH:3]=1.O[C@@H]1CN(C2C[CH2:55][O:54][CH2:53]C2)C[C@H]1NC(=O)CNC(=O)C1C=CC=C(C(F)(F)F)C=1.C(OC(NC1C(O)CN(C(OCC2C=CC=CC=2)=O)C1)=O)(C)(C)C.C(Br)C=C.C(Br)C1C=CC=CC=1>>[CH2:1]([O:8][C@@H:9]1[CH2:13][N:12]([CH:14]2[CH2:15][CH2:55][O:54][CH2:53][CH2:19]2)[CH2:11][C@H:10]1[NH:28][C:29](=[O:44])[CH2:30][NH:31][C:32](=[O:43])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:41])([F:40])[F:42])[CH:34]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 5

HCID 7498Benzyl BromideHCID 7841Allyl bromideHCID 66787842Benzyl 3-((tert-butoxycarbonyl)amino)-4-hydroxypyrrolidine-1-carboxylateHCID 67004726rel-N-(2-{[(3R,4R)-4-hydroxy-[1-tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamideHCID 67005044Rel-n-[2-({(3r,4r)-4-(benzyloxy)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide

Product 1

HCID 67005152Rel-n-(2-{[(3r,4r)-4-(allyloxy)-1-(tetrahydro-2h-pyran-4-yl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide

Procedure

The title compound was synthesized in similar fashion to rel-N-[2-({(3R,4R)-4-(benzyloxy)-1-[1-(6-methoxypyridin-3-yl)piperidin-4-yl]pyrrolidin-3-yl}amino)-2-oxoethyl]-3-(trifluoromethyl)benzamide, rel-N-(2-{[(3R,4R)-4-hydroxy-[1-tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide was substituted for benzyl rac-(3R,4R)-3-[(tert-butoxycarbonyl)amino]-4-hydroxypyrrolidine-1-carboxylate and allyl bromide was substituted for benzyl bromide. The title compound was isolated as a white solid. 1H-NMR (CDCl3) δ: 1.56 (m, 2H), 1.76 (m, 2H), 2.34-2.48 (m, 2H), 2.80 (m, 2H), 3.30-3.42 (m, 3H), 3.84 (m, 1H), 3.93-4.03 (m, 3H), 4.13 (m, 2H), 4.18 (m, 1H), 4.34 (m, 1H), 5.14 (m, 1H), 5.26 (m, 1H), 5.87 (m, 1H), 6.66 (b, 1H), 7.13 (b, 1H), 7.57 (t, J=7.4 Hz, 1H), 7.76 (d, J=7.6 Hz, 1H), 8.05 (d, J=7.7 Hz, 1H), 8.09 (s, 1H). MS m/z: 456 (M+1).

Sources & evidence

ORD record
ord-974d9cfea0f945049e9050aaf230fe25
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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