Lithium Hydroxide → HCID 117856476, compound

HRID 1497291Notes

Reaction equation

HRID 1497291 reaction equation
[F:1][CH:2]([F:15])[C@@H:3]1[C@@H:12]([OH:13])[C@H:11]([OH:14])[C@H:6]2[NH:7]C(=O)[O:9][C@H:5]2[CH2:4]1.[Li+].[OH-]>CO.O>[NH2:7][C@H:6]1[C@@H:5]([OH:9])[CH2:4][C@H:3]([CH:2]([F:1])[F:15])[C@@H:12]([OH:13])[C@@H:11]1[OH:14]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 71152424HCID 71152424, compound

Product 1

HCID 117856476HCID 117856476, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of (3aR,4R,5R,6S,7aS)-6-(difluoromethyl)-4,5-dihydroxyhexahydrobenzo[d]oxazol-2(3H)-one (255 mg, 1.48 mmol) in MeOH (2 mL) and water (3 mL) was added LiOH (600 mg, 25.0 mmol). The mixture was heated at reflux for 2 h. Solvents were evaporated and the residue was purified by silica gel column chromatography, eluted with 20% 2 M NH3 MeOH solution in DCM to give the product (1R,2R,3S,4S,6S)-3-amino-6-(difluoromethyl)cyclohexane-1,2,4-triol (214 mg, 99%) as a white solid. MS m/z 198.1 (M+1, 100%); 1H NMR (400 MHz, MeOD) δ 6.14 (t, J=57.2 Hz, 1H), 4.15 (br s, 1H), 3.63 (t, J=9.7 Hz, 1H), 3.30 (t, J=11.0 Hz, 1H), 2.91 (dd, J=10.4 Hz, 2.8 Hz, 1H), 2.20-2.36 (m, 1H), 1.97 (dt, J=14.4 Hz, 3.6 Hz, 1H), 1.53-1.60 (m, 1H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. customSolvents were evaporated
  4. customthe residue was purified by silica gel column chromatography
  5. washeluted with 20% 2 M NH3 MeOH solution in DCM

Sources & evidence

ORD record
ord-00b82109ea5b40a5aee3ac6fb4cbfce6
Source dataset
uspto-grants-2015_12
Patent number
US09199949B2

Reaction notes

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