HCID 10185831, compound → HCID 10301185, compound

HRID 1532979Notes

Reaction equation

HRID 1532979 reaction equation
[CH:1]1([C:6]2[C:15]([C:16](=[O:27])[C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)=[C:14]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[C:13]3[C:12](=[O:35])[CH2:11][C:10]([CH3:37])([CH3:36])[CH2:9][C:8]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>O1CCCC1>[CH:1]1([C:6]2[C:15]([C:16]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][CH:18]=3)=[O:27])=[C:14]([C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)[C:13]3[CH:12]([OH:35])[CH2:11][C:10]([CH3:37])([CH3:36])[CH2:9][C:8]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 10185831HCID 10185831, compound

Product 1

HCID 10301185HCID 10301185, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

625.3 g of 2-cyclopentyl-4-(4-fluorophenyl)-7,7-dimethyl-3-(4-trifluoromethylbenzoyl)-7,8-dihydro-6H-quinolin-5-one were reduced at 0° to −5° C. in 6 liters of tetrahydrofuran using 56.4 g of IR,2S-aminoindanol and 800 g of boranediethylaniline complex. Quenching of the reaction was carried out after approximately 20 hours using 500 ml of 1,2-ethanediol. The tetrahydrofuran was distilled off, the resulting oil was taken up in ethyl acetate and the organic phase was dried and concentrated after washing with 2 N hydrochloric acid and saturated sodium hydrogen carbonate solution. The residue was recrystallized hot from cyclohexane. A total of 574 g of colorless crystals having a purity of 99.4% according to HPLC (e.e. 97.4%) resulted.

Workup

  1. customQuenching of the reaction
  2. distillationThe tetrahydrofuran was distilled off
  3. customthe organic phase was dried
  4. concentrationconcentrated
  5. washafter washing with 2 N hydrochloric acid and saturated sodium hydrogen carbonate solution
  6. customThe residue was recrystallized hot from cyclohexane
  7. customresulted

Sources & evidence

ORD record
ord-6978967eba4345779e8bc976f44d62a5
Source dataset
uspto-grants-2001_03
Patent number
US06207671B1

Reaction notes

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