Triethylamine → (6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexyl)-carbamic acid 10,13-dimethyl-17-octyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

HRID 2403003Notes

Reaction equation

HRID 2403003 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[CH:12]([CH:13]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:14][CH:15]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[CH2:11][CH:10]([OH:38])[CH2:9]1.C(N([CH2:44][CH3:45])CC)C.[CH3:46][C@@H:47]([C@@H:54]1[C@@:58]2([CH3:76])[CH2:59][CH2:60][CH:61]3[C@@:66]4([CH3:75])[CH2:67][CH2:68][CH:69]([O:71][C:72](Cl)=[O:73])[CH2:70][C:65]4=[CH:64][CH2:63][CH:62]3[CH:57]2[CH2:56][CH2:55]1)CCCC(C)C.CO.C(Cl)(Cl)Cl>ClCCl>[CH3:75][C:66]12[CH2:67][CH2:68][CH:69]([O:71][C:72](=[O:73])[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][N:8]3[CH2:9][CH:10]([OH:38])[CH2:11][CH:12]3[CH:13]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[O:14][CH:15]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[CH2:70][C:65]1=[CH:64][CH2:63][CH:62]1[CH:61]2[CH2:60][CH2:59][C:58]2([CH3:76])[CH:57]1[CH2:56][CH2:55][CH:54]2[CH2:47][CH2:46][CH2:2][CH2:3][CH2:4][CH2:5][CH2:44][CH3:45]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 21584188Chloroform methanolHCID 54236888C28H45ClO2HCID 1317282151-(6-Amino-hexyl)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-pyrrolidin-3-ol

Product 1

HCID 131730805(6-{2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-pyrrolidin-1-yl}-hexyl)-carbamic acid 10,13-dimethyl-17-octyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl esterYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound 31 (4.5 g, 8.67 mmol) was dissolved in anhydrous dichloromethane (100 mL) and cooled to 0° C. To the solution were added triethylamine (2.52 g, 3.36 mL, 25 mmol) and cholesteryl chloroformate (3.89 g, 8.67 mmol) successively. The reaction temperature was brought to ambient temperature and stirred further for 2 h. The completion of the reaction was ascertained by TLC (10% MeOH/CHCl3). The reaction mixture was evaporated under the vacuum to afford the crude product. Compound 32 (3.05 g, 37%) was obtained as a white foamy solid after column chromatography over silica gel.

Workup

  1. customwas brought to ambient temperature
  2. customThe reaction mixture was evaporated under the vacuum
  3. customto afford the crude product

Sources & evidence

ORD record
ord-28c12ef5250546bd9a8396541693c054
Source dataset
uspto-grants-2014_08
Patent number
US08796436B2

Reaction notes

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