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 1055783Notes

Reaction equation

HRID 1055783 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-4635a6090a83420a931f9dbf3e58b15a
Source dataset
uspto-grants-2016_07
Patent number
US09394540B2

Reaction notes

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