1-(1,1-Dimethylethyl) 2-methyl (2R,4R)-4-hydroxy-1,2-piperidinedicarboxylate → HCID 58318653, compound

HRID 1027935Notes

Reaction equation

HRID 1027935 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@@H:4]([C:15]([O:17][CH3:18])=[O:16])[CH2:3]1.[Cl:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:31][CH3:32])=[C:27](O)[CH:28]=2)[N:23]=[CH:22][N:21]=1>>[Cl:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:31][CH3:32])=[C:27]([O:1][C@H:2]3[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[C@@H:4]([C:15]([O:17][CH3:18])=[O:16])[CH2:3]3)[CH:28]=2)[N:23]=[CH:22][N:21]=1

Participants

3

Reactant 2

HCID 70223581-(1,1-Dimethylethyl) 2-methyl (2R,4R)-4-hydroxy-1,2-piperidinedicarboxylateHCID 231324754-Chloro-7-methoxyquinazolin-6-ol

Product 1

HCID 58318653HCID 58318653, compound

Procedure

1-tert-butyl 2-methyl (2R,4R)-4-hydroxypiperidine-1,2-dicarboxylate (16) was coupled to 4-chloro-7-methoxyquinazolin-6-ol analogously as for the equivalent step in Example 7 to give 1-tert-butyl 2-methyl (2R,4S)-4-[(4-chloro-7-methoxyquinazolin-6-yl)oxy]piperidine-1,2-dicarboxylate (17): 1H NMR Spectrum: (DMSO-d6) δ1.39-1.46 (10H, m), 1.73-1.84 (1H, m), 1.92-2.03 (1H, m), 2.10-2.18 (1H, m), 2.60-2.69 (1H, m), 3.15-3.40 (3H, m), 3.74-3.85 (1H, m), 4.01 (3H, s), 4.61-4.73 (1H, m), 5.06 (1H, s), 7.43 (1H, s), 7.47 (1H, s), 8.89 (1H, s), 8.97 (1H, s); Mass Spectrum: (M+H)+ 452.

Sources & evidence

ORD record
ord-97703871e2f9483ba642822d0eeba1a1
Source dataset
uspto-grants-2014_05
Patent number
US08735410B2

Reaction notes

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