Dichloromethane → HCID 86732537, compound

HRID 1777010Notes

Reaction equation

HRID 1777010 reaction equation
C(N(C(C)C)C(C)C)C.Cl[CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:20][C:21]1[C:29]2[CH2:28][C:27]3([O:33][CH2:32][CH2:31][O:30]3)[CH2:26][CH2:25][C:24]=2[NH:23][N:22]=1.ClCCl>C(OCC)(=O)C>[CH2:13]([O:12][CH2:11][N:23]1[C:24]2[CH2:25][CH2:26][C:27]3([O:30][CH2:31][CH2:32][O:33]3)[CH2:28][C:29]=2[C:21]([CH3:20])=[N:22]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 137983Benzyl chloromethyl etherHCID 178434163HCID 178434163, compound

Product 1

HCID 86732537HCID 86732537, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-ethyl-N-isopropylpropan-2-amine (4.08 mL) and benzyl chloromethyl ether (0.792 mL) were added to a mixture of 3′-methyl-1′,4′,6′,7′-tetrahydrospiro[1,3-dioxolane-2,5′-indazole] (925 mg) and dichloromethane (20 mL) under ice cooling under an argon gas atmosphere, followed by stirring for 4.5 hours at room temperature. The reaction liquid was diluted with ethyl acetate and then washed with water, saturated aqueous sodium bicarbonate, and saturated brine in this order, followed by drying, and concentrating under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), thereby obtaining a mixture (1.11 g) of l′-[(benzyloxy)methyl]-3′-methyl-1′,4′,6′,7′-tetrahydrospiro[1,3-dioxolane-2,5′-indazole] and a regioisomer thereof.

Workup

  1. customThe reaction liquid
  2. washwashed with water, saturated aqueous sodium bicarbonate, and saturated brine in this order
  3. customby drying
  4. concentrationconcentrating under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7e2090b5c2aa40ec936e5a01bccb8fb7
Source dataset
uspto-grants-2016_02
Patent number
US09266840B2

Reaction notes

Loading…