HCID 68154265, compound → (4aR,5R,8S,8aR)-5-[(4-fluorophenyl)amino]-8-(hydroxymethyl)hexahydro-2H-chromen-4a(5H)-ol

HRID 73645Notes

Reaction equation

HRID 73645 reaction equation
[Si]([O:18][CH2:19][C@H:20]1[C@@H:29]2[C@:24]([OH:30])([CH2:25][CH2:26][CH2:27][O:28]2)[C@H:23]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[CH2:22][CH2:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:38][C:35]1[CH:34]=[CH:33][C:32]([NH:31][C@@H:23]2[CH2:22][CH2:21][C@@H:20]([CH2:19][OH:18])[C@@H:29]3[C@@:24]2([OH:30])[CH2:25][CH2:26][CH2:27][O:28]3)=[CH:37][CH:36]=1

Participants

3

Reactant 1

HCID 68154265HCID 68154265, compound

Product 1

HCID 68154051(4aR,5R,8S,8aR)-5-[(4-fluorophenyl)amino]-8-(hydroxymethyl)hexahydro-2H-chromen-4a(5H)-ol

Reagents, catalysts & solvents 1

HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

Dissolved 68 mg (4aS,5R,8S,8aR)-8-({[tert-butyl(diphenyl)silyl]oxy}methyl)-5-[(4-fluorophenyl)amino]hexahydro-2H-chromen-4a(5H)-ol in 4 mL tetrabutylammonium fluoride solution (2.0 M in THF) and stirred overnight at RT. Excess solvent was removed using a rotovap, then the residue was diluted with CH2Cl2, added to water, and extracted with CH2Cl2. The crude extract was dried over Na2SO4, filtered, concentrated, then purified on silica gel to provide the title compound. 1H NMR (500 MHz, CDCl3) δ=1.32-1.39 (m, 1H), 1.55-1.90 (m, 5H), 2.06-2.16 (m, 2H), 2.24-2.28 (m, 1H), 2.34-2.46 (m, 1H). 3.46 (s, 1H), 3.49-3.56 (m, 2H), 3.68-3.75 (m, 1H), 3.77-3.82 (m, 1H), 4.12 (dd, J1=11.4 Hz, J2=6.0 Hz, 1H), 4.64 (d, J=11.2 Hz), 6.50-6.56 (m, 2H), 6.85-6.90 (m, 2H) ppm.

Workup

  1. customExcess solvent was removed
  2. additionthe residue was diluted with CH2Cl2
  3. additionadded to water
  4. extractionextracted with CH2Cl2
  5. extractionThe crude extract
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified on silica gel

Sources & evidence

ORD record
ord-8265faaedc8a4238a6050e391f87e359
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

Loading…