Pentanal → 4-Chloro-6-methyl-10,10-dioxo-2-(4-pentyl-piperazin-1-yl)-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

HRID 1172507Notes

Reaction equation

HRID 1172507 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH3:5].[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]([CH3:35])[C:14]2[O:20][C:19]3[C:21]([Cl:31])=[CH:22][C:23]([N:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[CH:24][C:18]=3[CH2:17][S:16](=[O:33])(=[O:32])[C:15]=2[CH:34]=1)=[O:10].C([BH3-])#N.[Na+]>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]([CH3:35])[C:14]2[O:20][C:19]3[C:21]([Cl:31])=[CH:22][C:23]([N:25]4[CH2:26][CH2:27][N:28]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:29][CH2:30]4)=[CH:24][C:18]=3[CH2:17][S:16](=[O:32])(=[O:33])[C:15]=2[CH:34]=1)=[O:10]

Participants

6

Reactant 3

HCID 8063PentanalHCID 5003444Sodium cyanoborohydrideHCID 115410724-Chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cyclo heptene-8-carboxylic acid methyl ester

Product 1

HCID 1317284774-Chloro-6-methyl-10,10-dioxo-2-(4-pentyl-piperazin-1-yl)-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

Pentanaldehyde (0.042 gm, 0.5 mmol) was added with stirring to a solution of Example 104k (0.180 g, 0.4 mmol) in dry methanol (10 mL). Titanium isopropoxide (0.117 g, 0.4 mmol) was added and the reaction mixture was cooled to 10° C. Sodium cyanoborohydride (51 mg, 0.8 mmol) was added and the reaction mixture was heated at 60° C. overnight. It was concentrated, treated with water and extracted with n-butanol. The organic layer was washed with water, brine, concentrated and purified using flash chromatography (silica gel, 1-3% MeOH/CHCl3) to obtain the title compound. Yield: 0.2 g (99%), 1H NMR (CDCl3): δ 0.90 (s, 3H, CH3), 1.3 (t, 4H, 2CH2), 1.7 (t, 2H, CH2), 2.40 (t, 2H, CH2), 2.8 (t, 4H, 2CH2), 2.90 (s, 3H, CH3), 3.20 (t, 4H, 2CH2), 3.90 (s, 3H, CH3), 4.8 (s, 2H, CH2), 6.70 (s, 1H, Ar), 6.90 (s, 1H, Ar), 8.1 (s 1H, Ar), 8.4 (s 1H, Ar); MS: m/e (EI+) 507 (M+1).

Workup

  1. temperaturethe reaction mixture was heated at 60° C. overnight
  2. concentrationIt was concentrated
  3. additiontreated with water
  4. extractionextracted with n-butanol
  5. washThe organic layer was washed with water, brine
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-d0135877e2e24ce5a9566b30b0c73336
Source dataset
uspto-grants-2010_11
Patent number
US07834001B2

Reaction notes

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