Diisopropylethylamine → 4-{3-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-ylcarbamoyl]-5-methoxy-phenoxy}-butyric acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[C:12]([C:14](=[O:22])[NH:15][CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:11]=[C:10]([O:23][CH3:24])[CH:9]=1.C(OC(N1CCC(NC(=O)C2C=C(OCCCC(OC)=O)C=C(OC)C=2)CC1)=O)(C)(C)C.[CH2:58]([O:60][C:61]1[CH:62]=[C:63]([CH:66]=[C:67]([O:70][CH2:71][CH3:72])[C:68]=1[F:69])[CH:64]=O)[CH3:59].C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([O:23][CH3:24])[CH:11]=[C:12]([C:14](=[O:22])[NH:15][CH:16]2[CH2:17][CH2:18][N:19]([CH2:64][C:63]3[CH:66]=[C:67]([O:70][CH2:71][CH3:72])[C:68]([F:69])=[C:61]([O:60][CH2:58][CH3:59])[CH:62]=3)[CH2:20][CH2:21]2)[CH:13]=1Participants
8
Reactant 5
HCID 81531Diisopropylethylamine
HCID 5003444Sodium cyanoborohydride
HCID 591282733,5-Diethoxy-4-fluoro-benzaldehyde
HCID 684579394-[3-Methoxy-5-(piperidin-4-ylcarbamoyl)-phenoxy]-butyric acid methyl ester
HCID 684598954-[3-Methoxy-5-(3-methoxycarbonyl-propoxy)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl esterProduct 1
Reagents, catalysts & solvents 2
Procedure
In analogy to the procedure described in example 50k), 4-[3-methoxy-5-(piperidin-4-ylcarbamoyl)-phenoxy]-butyric acid methyl ester [prepared from 4-[3-methoxy-5-(3-methoxycarbonyl-propoxy)-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester by Boc cleavage in analogy to example 50i)] was reacted with 3,5-diethoxy-4-fluoro-benzaldehyde (example 50 g), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless solid. MS: 547.3 (MH+).
Sources & evidence
- ORD record
- ord-d64a5006042f4d14b04a29ff23e2f178
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772253B2
Reaction notes
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