Diisopropylethylamine → Rac-3-(2,3-dihydroxy-propoxy)-n-[1-(3,5-diisopropoxy-benzyl)-piperidin-4-yl]-5-methoxy-benzamide

HRID 502438Notes

Reaction equation

HRID 502438 reaction equation
FC(F)(F)C(O)=O.[OH:8][CH:9]([CH2:29][OH:30])[CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:24]=[C:25]([O:27][CH3:28])[CH:26]=1)[C:15]([NH:17][CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:16].[CH:31]([O:34][C:35]1[CH:36]=[C:37]([CH:40]=[C:41]([O:43][CH:44]([CH3:46])[CH3:45])[CH:42]=1)[CH:38]=O)([CH3:33])[CH3:32].C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.C(O)(=O)C>[OH:8][CH:9]([CH2:29][OH:30])[CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:24]=[C:25]([O:27][CH3:28])[CH:26]=1)[C:15]([NH:17][CH:18]1[CH2:23][CH2:22][N:21]([CH2:38][C:37]2[CH:40]=[C:41]([O:43][CH:44]([CH3:46])[CH3:45])[CH:42]=[C:35]([O:34][CH:31]([CH3:33])[CH3:32])[CH:36]=2)[CH2:20][CH2:19]1)=[O:16]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 113106053,5-DiisopropoxybenzaldehydeHCID 68458548rac-3-(2,3-Dihydroxy-propoxy)-5-methoxy-N-piperidin-4-yl-benzamide trifluoroacetate

Product 1

HCID 68457139Rac-3-(2,3-dihydroxy-propoxy)-n-[1-(3,5-diisopropoxy-benzyl)-piperidin-4-yl]-5-methoxy-benzamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 50k), crude rac-3-(2,3-dihydroxy-propoxy)-5-methoxy-N-piperidin-4-yl-benzamide trifluoroacetate was reacted with 3,5-diisopropoxy-benzaldehyde (example 126b), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless amorphous solid. MS: 531.3 (MH+).

Sources & evidence

ORD record
ord-492981eeb3c9498380dc3350bc6ad699
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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