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

HRID 1927494Notes

Reaction equation

HRID 1927494 reaction equation
[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[CH3:12][O:13][C:14]([C:16]1[CH:17]=[C:18]([CH3:40])[C:19]2[O:25][C:24]3[C:26]([Cl:36])=[CH:27][C:28]([N:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)=[CH:29][C:23]=3[CH2:22][S:21](=[O:38])(=[O:37])[C:20]=2[CH:39]=1)=[O:15].C([BH3-])#N.[Na+]>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:12][O:13][C:14]([C:16]1[CH:17]=[C:18]([CH3:40])[C:19]2[O:25][C:24]3[C:26]([Cl:36])=[CH:27][C:28]([N:30]4[CH2:31][CH2:32][N:33]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])[CH2:34][CH2:35]4)=[CH:29][C:23]=3[CH2:22][S:21](=[O:37])(=[O:38])[C:20]=2[CH:39]=1)=[O:15]

Participants

6

Reactant 3

HCID 8175DecanalHCID 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 1317284764-Chloro-2-(4-decyl-piperazin-1-yl)-6-methyl-10,10-dioxo-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

Decanaldehyde (0.071 g, 0.45 mmol) was added with stirring to a solution of Example 104k (0.2 g, 0.45 mmol) in dry methanol (5 mL). Titanium isopropoxide (0.12 g, 0.45 mmol) was added and the reaction mixture was cooled to 10° C. Sodium cyanoborohydride (0.057 g, 0.9 mmol) was added and the reaction mixture was refluxed for 2 h. 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, MeOH/CHCl3) to obtain the title compound. Yield: 0.120 g (46%); 1H NMR (CDCl3): δ 0.90 (s, 5H, CH3CH2), 1.20 (m, 12H, 6CH2), 2.28 (s, 4H, 2CH2), 2.30 (t, 2H, CH2), 2.70 (t, 3H, CH3), 3.20 (t, 4H, 2CH2), 3.90 (s, 3H, OCH3), 4.80 (s, 2H, CH2), 6.80 (s, 1H, Ar), 7.00 (s, 1H, Ar), 8.10 (s, 1H, Ar), 8.4 (s 1H Ar); MS: M/e (EI+) 577 (M+1).

Workup

  1. temperaturethe reaction mixture was refluxed for 2 h
  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-f977038259974abcbc0b1e70560441a5
Source dataset
uspto-grants-2012_05
Patent number
US08183234B2

Reaction notes

Loading…