Diazomethane → HCID 19874697, compound

HRID 1494060Notes

Reaction equation

HRID 1494060 reaction equation
[O:1]=[C:2]([CH3:9])[CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].Br[CH2:11][C:12]#[N:13].[K].[CH3:15][Si](C)(C)N[Si](C)(C)C.[N+](=C)=[N-].[BH4-].[Na+]>>[C:12]([CH2:11][CH2:9][CH:2]([OH:1])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:15])=[O:7])#[N:13]

Participants

7

Reactant 6

HCID 9550DiazomethaneHCID 11534BromoacetonitrileHCID 13838HexamethyldisilazaneHCID 184074-Acetylbutyric acidHCID 4311764Sodium borohydrideHCID 5462222Potassium

Product 1

HCID 19874697HCID 19874697, compound

Procedure

Hex-5-enoic acid is first converted to the corresponding epoxide with e.g. m-chloroperbenzoic acid and esterified with diazomethane to the methyl ester which is then condensed with acetonitrile in the presence of lithium diisopropylamide (LDA) to yield methyl 7-cyano-5-hydroxyheptanoate. Alternatively, 5-oxohexanoic acid is condensed with bromoacetonitrile in the presence of e.g. the potassium salt of hexamethyl disilazane, followed by esterification with e.g. diazomethane and reduction with sodium borohydride to yield methyl 7-cyano-5-hydroxyheptanoate. Condensation with 3-hydroxypyridine in the presence of triphenylphosphine and reduction of the nitrile yields methyl 8-amino-5-(3-pyridyloxy)-octanoate.

Sources & evidence

ORD record
ord-506002288c7341868d2a963f197aafa7
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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