Beta-Alanine → HCID 18344923, compound

HRID 917305Notes

Reaction equation

HRID 917305 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[CH2:7](N(CC)CC)[CH3:8].[CH3:14][CH2:15][CH2:16][C:17](=O)[CH2:18][CH2:19][CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)C.ClCCl>[CH2:7]([O:5][C:4](=[O:6])[CH2:3][CH2:2][NH:1][CH:17]([CH2:18][CH2:19][CH3:20])[CH2:16][CH2:15][CH3:14])[CH3:8]

Participants

7

Reactant 4

HCID 239Beta-AlanineHCID 8471TriethylamineHCID 312464-HeptanoneHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18344923HCID 18344923, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a 12 L 3-neck flask equipped with a mechanical stirrer and nitrogen inlet was charged 400 g (2.6 mol) of β-alanine, 2250 L of dichloromethane and 2.3 L of ethanol. Agitation was begun and 1.09 L (7.8 mol, 3 eq) of triethyl amine and 364 mL (2.6 mol, 1 eq) of 4-heptanone were added. The mixture was cooled to <10° C. and 1.65 Kg (7.8 mol, 3 eq) of sodium triacetoxy borohydride. Mixture kept <15° C. and stirred for 24 hrs.

Workup

  1. customTo a 12 L 3-neck flask equipped with a mechanical stirrer and nitrogen inlet
  2. temperatureThe mixture was cooled to <10° C.
  3. customkept <15° C.

Sources & evidence

ORD record
ord-901913d68ad4477fbe63735feff77035
Source dataset
uspto-grants-2007_09
Patent number
US07273871B2

Reaction notes

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