Hexane → HCID 87160551, compound

HRID 2206897Notes

Reaction equation

HRID 2206897 reaction equation
[F:1][C:2]([F:40])([F:39])[C:3]1[CH:4]=[C:5]([C:13]2([C:35]([F:38])([F:37])[F:36])[CH2:17][CH2:16][N:15]([C:18]3[CH:32]=[CH:31][C:21]([CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[C:20]([Cl:33])[CH:19]=3)[C:14]2=[O:34])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CCCCCC.[H-].C([Al+]CC(C)C)C(C)C.C(O)C.C(=O)=O>ClCCl.C(OCC)(=O)C>[F:40][C:2]([F:1])([F:39])[C:3]1[CH:4]=[C:5]([C:13]2([C:35]([F:36])([F:37])[F:38])[CH2:17][CH2:16][N:15]([C:18]3[CH:32]=[CH:31][C:21]([CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[C:20]([Cl:33])[CH:19]=3)[CH:14]2[OH:34])[CH:6]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:8]=1

Participants

7

Reactant 4

HCID 8058Hexane2×HCID 19604758Methanedione--ethanol (1/1)HCID 21225700Diisobutylaluminumhydride2×HCID 87160553HCID 87160553, compound

Product 1

HCID 87160551HCID 87160551, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tert-butyl (4-{3-[3,5-bis(trifluoromethyl)phenyl]-2-oxo-3-(trifluoro-methyl)-pyrrolidin-1-yl}-2-chloro-benzyl)carbamate (0.36 g) was dissolved in dichloromethane (6 mL). To the resulting solution was slowly added n-hexane solution (1.8 mL) of 1 mol/l diisobutylaluminum hydride while being cooled with ethanol-dry ice under argon atmosphere, and stirring was continued for 30 minutes at the same temperature. Then, n-hexane solution (0.6 mL) of 1 mol/l diisobutylaluminum hydride was further added thereto, and stirring was continued for 30 minutes at the same temperature. Ethyl acetate (1.2 mL) was added, the ethanol-dry ice bath was removed, and stirring was continued for 1 hour. Sodium sulfate decahydrate (3.8 g) was added and stirring was continued for 30 minutes. The precipitates were filtered using Celite and washed with ethyl acetate. The collected filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was separated and purified by column chromatography to obtain tert-butyl (4-{3-[3,5-bis(trifluoromethyl)phenyl]-2-hydroxy-3-(trifluoromethyl)pyrrolidin-1-yl}-2-chlorobenzyl)carbamate (0.30 g).

Workup

  1. stirringstirring
  2. waitwas continued for 30 minutes at the same temperature
  3. customthe ethanol-dry ice bath was removed
  4. stirringstirring
  5. waitwas continued for 1 hour
  6. additionSodium sulfate decahydrate (3.8 g) was added
  7. stirringstirring
  8. waitwas continued for 30 minutes
  9. filtrationThe precipitates were filtered
  10. washwashed with ethyl acetate
  11. concentrationThe collected filtrate was concentrated under reduced pressure
  12. customto obtain a crude product
  13. customThe crude product was separated
  14. custompurified by column chromatography

Sources & evidence

ORD record
ord-6182ba3ace4f4a38933aaee5af89de17
Source dataset
uspto-grants-2016_06
Patent number
US09375000B2

Reaction notes

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