Dimethylamine → HCID 135955761, compound

HRID 1881358Notes

Reaction equation

HRID 1881358 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([CH:9]([CH3:11])[CH3:10])=[CH:4][C:3]=1[C:12]1[N:16]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[CH2:22][C:21](=O)[CH2:20]3)[C:15](S)=[N:14][N:13]=1.[CH3:28][NH:29][CH3:30].[BH-](OC(C)=O)(OC(C)=O)[O:32]C(C)=O.[Na+].O>C1COCC1.CC(O)=O>[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([CH:9]([CH3:10])[CH3:11])=[CH:4][C:3]=1[C:12]1[N:16]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[CH2:22][CH:21]([N:29]([CH3:30])[CH3:28])[CH2:20]3)[C:15](=[O:32])[NH:14][N:13]=1

Participants

7

Reactant 4

HCID 674DimethylamineHCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 178438839HCID 178438839, compound

Product 1

HCID 135955761HCID 135955761, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 11 (340 mg, 0.9 mmol) was dissolved in THF (4 mL). AcOH (2 drops, cat. amount) was added followed by dimethylamine in THF (1N solution, 0.7 mL, 1.35 mmol). NaBH(OAc)3 (286 mg, 1.35 mmol) was added to the reaction mixture and the reaction mixture was stirred at room temperature for 30 min. Water was added and the reaction mixture was extracted with EtOAc. Combined organic layers were washed with water and brine and dried over Na2SO4. Purification of the concentrated crude product by column chromatography (MeOH: CH2Cl2=2:8) afforded the title product as a pale yellow solid (80 mg, 25%).

Workup

  1. extractionthe reaction mixture was extracted with EtOAc
  2. washCombined organic layers were washed with water and brine
  3. dry with materialdried over Na2SO4
  4. customPurification of the
  5. concentrationconcentrated crude product by column chromatography (MeOH: CH2Cl2=2:8)

Sources & evidence

ORD record
ord-6c7e53fcbc684be384207004bf54aa04
Source dataset
uspto-grants-2012_11
Patent number
US08318790B2

Reaction notes

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