Acetic Acid → HCID 69652704, compound

HRID 1831748Notes

Reaction equation

HRID 1831748 reaction equation
C(Cl)(=O)C(Cl)=O.[Cl:7][C:8]1[C:17]([CH2:18][CH2:19]O)=[CH:16][C:15]2[NH:14][C:13](=[O:21])[CH:12]3[CH2:22][CH2:23][CH2:24][CH:11]3[C:10]=2[CH:9]=1.C(N(CC)CC)C.[Cl:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=1)[CH2:36][NH2:37].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.CS(C)=O.ClCCl.C(OCC)(=O)C.C1COCC1>[Cl:7][C:8]1[C:17]([CH2:18][CH2:19][NH:37][CH2:36][C:35]2[CH:38]=[CH:39][CH:40]=[C:33]([Cl:32])[CH:34]=2)=[CH:16][C:15]2[NH:14][C:13](=[O:21])[CH:12]3[CH2:22][CH2:23][CH2:24][CH:11]3[C:10]=2[CH:9]=1

Participants

12

Reactant 6

HCID 176Acetic AcidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 77802Benzenemethanamine, 3-chloro-HCID 5049666Sodium triacetoxyborohydrideHCID 53951689HCID 53951689, compound

Product 1

HCID 69652704HCID 69652704, compoundYield 55.4%

Reagents, catalysts & solvents 5

HCID 111,2-DichloroethaneSolvent3×HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

0.22 ml (3.12 mmol) of DMSO in 2 ml of 1,2-dichlorethane is added in drops to a solution of 0.18 ml (2.04 mmol) of oxalyl chloride in 4 ml of 1,2-dichloroethane at −70° C. After 10 minutes at −70° C., a solution of 270 mg (1.02 mmol) of 8-chloro-7-hydroxyethyl-1,2,3,3a,5,9b-hexahydrocyclopenta[c]quinolin-4-one in 5 ml of 1,2-dichloroethane and 2 ml of DMSO are added in drops to it. After 2 hours at −70° C., the batch is diluted with 30 ml of dichloromethane and stirred for 3 hours at −70° C. After 1.27 ml (9.18 mmol) of triethylamine is added, the reaction solution is stirred for 1 hour at room temperature and concentrated by evaporation in a vacuum. The residue is taken up in 20 ml of 1,2-dichloroethane and 20 ml of THF and mixed with 0.14 ml (1.53 mmol) of 3-chlorobenzylamine, 323 mg (1.53 mmol) of sodium (triacetoxy)borohydride and 0.6 ml (10.2 mmol) of acetic acid. After 24 hours at room temperature, the batch is diluted with ethyl acetate, washed with water, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with dichloromethane-methanol yields 220 mg of product.

Workup

  1. waitAfter 2 hours at −70° C.
  2. stirringthe reaction solution is stirred for 1 hour at room temperature
  3. concentrationconcentrated by evaporation in a vacuum
  4. waitAfter 24 hours at room temperature
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-4c3946a27bd04161880c7e47d48bdefd
Source dataset
uspto-grants-2006_06
Patent number
US07067667B2

Reaction notes

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