Sodium triacetoxyborohydride → 2-{2-[(Adamantan-1-ylmethyl)-amino]4-bromo-phenyl}-malonic acid di-tert-butyl ester

HRID 1355670Notes

Reaction equation

HRID 1355670 reaction equation
[C:1]12([CH:11]=O)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:13]([O:17][C:18](=[O:35])[CH:19]([C:27]1[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][C:28]=1[NH2:34])[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([CH3:16])([CH3:15])[CH3:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[C:13]([O:17][C:18](=[O:35])[CH:19]([C:27]1[CH:32]=[CH:31][C:30]([Br:33])=[CH:29][C:28]=1[NH:34][CH2:11][C:1]12[CH2:10][CH:5]3[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]3)[CH2:8]1)[CH2:2]2)[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])([CH3:14])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 110410501-AdamantanecarboxaldehydeHCID 700318672-(2-Amino-4-bromo-phenyl)-malonic acid di-tert-butyl ester

Product 1

HCID 700344512-{2-[(Adamantan-1-ylmethyl)-amino]4-bromo-phenyl}-malonic acid di-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of adamantane-1-carbaldehyde (3.77 g, 23 mmol) in acetic acid (45 ml) was added 2-(2-amino-4-bromo-phenyl)-malonic acid di-tert-butyl ester (4.44 g, 11.5 mmol) followed by addition of sodium triacetoxyborohydride (3.41 g, 16 mmol). The reaction mixture stirred for 30 minutes. After removal of the acetic acid, the reaction mixture was then partitioned between water and chloroform. Powdered K2CO3 was added and the pH of the aqueous layer was adjusted to 8. After separation, the organic layer was then washed with brine, dried over MgSO4, filtered and concentrated under vacuum to give the crude title compound of 9A as a brown oil (7.81 9), which was used in the next step without further purification.

Workup

  1. customAfter removal of the acetic acid
  2. customthe reaction mixture was then partitioned between water and chloroform
  3. additionPowdered K2CO3 was added
  4. customAfter separation
  5. washthe organic layer was then washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0c59108801aa4252b7e40e264ab3cfb2
Source dataset
uspto-grants-2003_07
Patent number
US06586447B1

Reaction notes

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