Diisopropylethylamine → Rac-n-[1-(2,6-diethoxy-4'-fluoro-biphenyl-4-ylmethyl)-piperidin-4-yl]-3-(2,3-dihydroxy-propoxy)-5-methoxy-benzamide

HRID 502458Notes

Reaction equation

HRID 502458 reaction equation
Cl[C:2]1[C:31]([O:32][CH2:33][CH3:34])=[CH:30][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:29])[C:15]3[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH2:24][CH:25]([OH:28])[CH2:26][OH:27])[CH:16]=3)[CH2:9][CH2:8]2)=[CH:4][C:3]=1[O:35][CH2:36][CH3:37].C(OC1C=C(C=O)C=C(OCC)C=1[C:52]1[CH:57]=[CH:56][C:55]([F:58])=[CH:54][CH:53]=1)C.C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.C(O)(=O)C>[CH2:36]([O:35][C:3]1[CH:4]=[C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([NH:13][C:14](=[O:29])[C:15]3[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:23][CH2:24][CH:25]([OH:28])[CH2:26][OH:27])[CH:16]=3)[CH2:9][CH2:8]2)[CH:30]=[C:31]([O:32][CH2:33][CH3:34])[C:2]=1[C:52]1[CH:57]=[CH:56][C:55]([F:58])=[CH:54][CH:53]=1)[CH3:37]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 593831002,6-Diethoxy-4'-fluoro-biphenyl-4-carbaldehydeHCID 68455978HCID 68455978, compound

Product 1

HCID 68454650Rac-n-[1-(2,6-diethoxy-4'-fluoro-biphenyl-4-ylmethyl)-piperidin-4-yl]-3-(2,3-dihydroxy-propoxy)-5-methoxy-benzamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 50k), rac-3-(2,3-dihydroxy-propoxy)-5-methoxy-N-piperidin-4-yl-benzamide hydrochloride (example 248) was reacted with 2,6-diethoxy-4′-fluoro-biphenyl-4-carbaldehyde (example 102), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless solid. MS: 597.3 (MH+).

Sources & evidence

ORD record
ord-6e87a855f1ec40c9a9dd626004630266
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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