Dimethylformamide → HCID 71767643, compound

HRID 1771434Notes

Reaction equation

HRID 1771434 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][C@@H:8]([CH3:20])[O:9][CH:10]2[C:15](OCC)=O)[CH3:4].C[N:22]([CH:24]=O)[CH3:23].IC.CCOC(C)=O.C(Cl)Cl.[CH2:37]([N:39](CC)CC)C>>[CH2:3]([C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][C@@H:8]([CH3:20])[O:9][C:10]2([C:23]1[NH:39][CH2:37][CH2:24][N:22]=1)[CH3:15])[CH3:4]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22169412HCID 22169412, compoundHCID 131734655HCID 131734655, compound

Product 1

HCID 71767643HCID 71767643, compound

Procedure

The mixture of NaH (0.39 g), (3R)-ethyl 5-ethyl-3-methylisochroman-1-carboxylate (0.6 g) and DMF (7 ml) was stirred for 2 hrs in ice-bath temperature. Iodomethane (1.5 ml) was added and the mixture was stirred at ambient temperature for 16 hrs. The intermediate (3R)-ethyl 5-ethyl-1,3-dimethylisochroman-1-carboxylate (0.5 g) was purified with separation method A and the title compound was synthesized using the procedure of synthesis method A step 3 and separation method E (EtOAc/DCM/triethyl amine 10/20/1). (Yield 0.06 g).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 16 hrs
  2. customThe intermediate (3R)-ethyl 5-ethyl-1,3-dimethylisochroman-1-carboxylate (0.5 g) was purified with separation method A

Sources & evidence

ORD record
ord-faeae7c6c41d4dea80637956254a655c
Source dataset
uspto-grants-2016_02
Patent number
US09249127B2

Reaction notes

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