HCID 71152401, compound → HCID 117857041, compound

HRID 1497280Notes

Reaction equation

HRID 1497280 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@H:14]2[NH:15]C(=O)[O:17][C@H:13]2[CH2:12][C@H:11]([CH2:19][F:20])[C@H:10]1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.O.[OH-].[Na+]>[NH2:15][C@@H:14]1[C@@H:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:10]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C@@H:11]([CH2:19][F:20])[CH2:12][C@@H:13]1[OH:17]

Participants

5

Reactant 1

HCID 71152401HCID 71152401, compound

Product 1

HCID 117857041HCID 117857041, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of (3aS,4R,5R,6S,7aS)-4,5-bis(benzyloxy)-6-(fluoromethyl)hexahydrobenzo[d]oxazol-2(3H)-one (410 mg, 1.065 mmol) in ethanol (8 mL), water (8 mL) and 5 N NaOH (4 mL) was heated at reflux for 2 h. After cooling, the reaction was diluted with water (50 mL), extracted with DCM (3×25 mL) and dried with Na2SO4. The solvent was evaporated to give (1S,2S,3R,4R,5S)-2-amino-3,4-bis(benzyloxy)-5-(fluoromethyl)cyclohexanol as a white solid (370 mg, 97%) which was pure enough for next reaction. MS m/z 382.2 (M+23, 100%); 1H NMR (400 MHz, CDCl3) δ 7.29-7.39 (m, 10H), 5.03 (d, J=11.4 Hz, 1H), 4.91 (d, J=10.9 Hz, 1H), 4.78 (ddd, J=48.0 Hz, 9.0 Hz, 3.0 Hz, 1H), 4.67 (d, J=10.9 Hz, 1H), 4.65 (d, J=11.4 Hz, 1H), 4.37 (ddd, J=47.4 Hz, 9.1 Hz, 2.0 Hz, 1H), 3.88 (br s, 1H), 3.58 (t, J=9.4 Hz, 1H), 3.48 (t, J=9.9 Hz, 1H), 2.11-2.26 (m, 1H), 1.95 (dt, J=14.3 Hz, 3.1 Hz, 1H), 1.63 (t, J=13.6 Hz, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperatureAfter cooling
  4. extractionextracted with DCM (3×25 mL)
  5. dry with materialdried with Na2SO4
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c168e5b294c942d796446becfe359670
Source dataset
uspto-grants-2015_12
Patent number
US09199949B2

Reaction notes

Loading…