Dichloromethane → HCID 57803525, compound

HRID 2102999Notes

Reaction equation

HRID 2102999 reaction equation
[Cl:1][C:2]1(C)[C:14]([CH3:15])=[C:13]2[C:5]([CH2:6][CH2:7][C:8]3([O:12]2)[CH2:11][CH2:10][CH2:9]3)=[CH:4][CH:3]1[OH:16].Cl.[CH3:19][N:20]([CH2:22][C:23](Cl)=[O:24])[CH3:21].Cl[CH2:27]Cl>C(OCC)(=O)C>[CH3:19][N:20]([CH2:22][C:23]([O:16][C:3]1[C:4]([CH3:27])=[C:5]2[C:13](=[C:14]([CH3:15])[C:2]=1[Cl:1])[O:12][C:8]1([CH2:11][CH2:10][CH2:9]1)[CH2:7][CH2:6]2)=[O:24])[CH3:21]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 139949912-(Dimethylamino)acetyl chloride hydrochlorideHCID 69056848HCID 69056848, compound

Product 1

HCID 57803525HCID 57803525, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-chloro-7,8-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol (300 mg), prepared as described above, and dimethylaminoacetyl chloride hydrochloride (564 mg) in dichloromethane (8 mL) was added N-ethyldiiospropylamine (1.4 mL) dropwise at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 16 hours. The solution was diluted with ethyl acetate and washed with water and brine, dried and evaporated. Chromatography (silica gel, hexane-ethyl acetate 5% to 25%) gave 276 mg of 7-chloro-5,8-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-yl (dimethylamino)acetate.

Workup

  1. additionwas added N-ethyldiiospropylamine (1.4 mL) dropwise at room temperature under nitrogen
  2. washwashed with water and brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-e78e3818a3bd48f69f79484cd028c24e
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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