Acetaldehyde, 2,2-dimethoxy- → HCID 68689040, compound

HRID 1159024Notes

Reaction equation

HRID 1159024 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12].[CH3:14][O:15][CH:16]([O:19][CH3:20])[CH:17]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CCOC(C)=O>[CH3:14][O:15][CH:16]([O:19][CH3:20])[CH2:17][NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:13])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12]

Participants

6

Reactant 3

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 5049666Sodium triacetoxyborohydrideHCID 11116645HCID 11116645, compound

Product 1

HCID 68689040HCID 68689040, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(2-aminoethyl)-2-hydroxybenzamide (332 mg, 1.85 mmol), dimethoxyacetaldehyde (0.475 mL, 1.85 mmol) in CH2Cl2 (10 mL) was added sodium triacetoxyboro hydrid (588 mg, 2.80 mmol). The resulting mixture was stirred overnight, then diluted with EtOAc (50 mL), washed with 10 mL of water and then brine, dried over MgSO4, and conc in vacuo to yield 441 mg (97%) of the product as a colorless oil. MS (ESI) 269 (M+H).

Workup

  1. washwashed with 10 mL of water
  2. dry with materialbrine, dried over MgSO4

Sources & evidence

ORD record
ord-c7230e6dc00743efbefbb2c56fdc2421
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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