2-Acetylpyridine → Hydrochloric Acid

HRID 1785417Notes

Reaction equation

HRID 1785417 reaction equation
C(OC(NCCN(C1C=C(C)C=CC=1C#N)CCNC(OC(C)(C)C)=O)=O)(C)(C)C.[ClH:31].CCOCC.[C:37]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=1)(=[O:39])C.[BH4-:46].[Na+:47]>CO>[N:41]1[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=1[CH:37]=[O:39].[BH4-:46].[Na+:47].[ClH:31]

Participants

8

Reactant 4

HCID 142862-AcetylpyridineHCID 4311764Sodium borohydrideHCID 10953452Ether hydrochlorideHCID 69032449Bis(2-tert-butoxycarbonylaminoethyl)amino-4-methylphenylcyanide

Product 3

HCID 313Hydrochloric AcidHCID 142732-PyridinecarboxaldehydeHCID 4311764Sodium borohydride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The resultant bis(2-tert-butoxycarbonylaminoethyl)amino-4-methylphenylcyanide was deprotected using HCl/ether, condensed with 2-acetyl pyridine (0.01 mol) in MeOH, and then reduced by NaBH4. After sequential treatments with pyridine-2-carboxaldehyde, NaBH4, and HCl, compound 110 was obtained in 75% overall yield.

Sources & evidence

ORD record
ord-c001bf39cddb49e79b8162bc550037a2
Source dataset
uspto-grants-2009_03
Patent number
US07504422B2

Reaction notes

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