Formaldehyde → HCID 58043985, compound

HRID 1919074Notes

Reaction equation

HRID 1919074 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH2:17][NH:16][CH2:15][CH2:14]3)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.C=O.[BH3-][C:24]#N.[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[CH:12]=[C:13]3[C:18](=[CH:19][CH:20]=2)[CH2:17][N:16]([CH3:24])[CH2:15][CH2:14]3)[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 58044158HCID 58044158, compound

Product 1

HCID 58043985HCID 58043985, compoundYield 86.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

A 100 mL round bottom flask with a magnetic stirrer was charged with 258b (350 mg, 0.8 mmol), formaldehyde (37% aqueous soln, 4.1 mmol), NaBH3CN (150 mg, 2.4 mmol), ZnCl2 (170 mg, 1.2 mmol) in methanol (46 mL). The mixture was stirred for 16 h at room temperature. After this time, the mixture was concentrated under reduced pressure and 10% aqueous K2CO3 (25 mL). The desired product crashed out of this mixture and was filtered. Upon washing with diethyl ether (20 mL) afforded a 85% yield (240 mg) of 266a.

Workup

  1. concentrationAfter this time, the mixture was concentrated under reduced pressure and 10% aqueous K2CO3 (25 mL)
  2. filtrationwas filtered
  3. washUpon washing with diethyl ether (20 mL)

Sources & evidence

ORD record
ord-23b277af463c414a8f0a06b9faf586fd
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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