Methanol → [2-Fluoro-4-(4-hydroxy-cyclohex-1-enyl)-phenyl]-carbamic acid benzyl ester

HRID 1027410Notes

Reaction equation

HRID 1027410 reaction equation
[CH2:1]([O:8][C:9](=[O:32])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH2:22][CH2:21][CH:20]([O:23][Si](C(C)(C)C)(C)C)[CH2:19][CH:18]=2)=[CH:13][C:12]=1[F:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].CO>C1COCC1.C(Cl)Cl.CCOC(C)=O>[CH2:1]([O:8][C:9](=[O:32])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH:18]=2)=[CH:13][C:12]=1[F:31])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 2724141Tetrabutylammonium FluorideHCID 67479117{4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-2-fluoro-phenyl}-carbamic acid benzyl ester

Product 1

HCID 67479441[2-Fluoro-4-(4-hydroxy-cyclohex-1-enyl)-phenyl]-carbamic acid benzyl esterYield 92%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

{4-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-2-fluoro-phenyl}-carbamic acid benzyl ester (340 mg, 0.75 mmol) was dissolved in THF (10 mL). To this solution at rt was added TBAF (1M in THF) (2 mL, 2 mmol). The reaction mixture was stirred at rt overnight. After the reaction was complete (TLC, 5% MeOH in DCM), the reaction was diluted with EtOAc (5 mL), quenched with NaHCO3 (saturated, 5 mL). The two layers were separated and the aq. layer was extracted with EtOAc (15 mL×2). The EtOAc solution was combined, washed with NaHCO3 aq, and brine (10 mL each), sequentially, and dried over K2CO3, filtered, concentrated. The crude product was purified on a silica gel column, eluted with 5% MeOH in DCM to obtain 230 mg (92% yield) of the title compound as a tan solid.

Workup

  1. customquenched with NaHCO3 (saturated, 5 mL)
  2. customThe two layers were separated
  3. extractionthe aq. layer was extracted with EtOAc (15 mL×2)
  4. washwashed with NaHCO3 aq, and brine (10 mL each)
  5. dry with materialsequentially, and dried over K2CO3
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified on a silica gel column
  9. washeluted with 5% MeOH in DCM

Sources & evidence

ORD record
ord-d08ede4d626f43f9bfd6621d2919346e
Source dataset
uspto-grants-2014_05
Patent number
US08735385B2

Reaction notes

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