Tetrahydrofuran → HCID 96930706, compound

HRID 1507201Notes

Reaction equation

HRID 1507201 reaction equation
[OH-].[K+].O1CCCC1.[CH2:8]([O:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH:23]2[O:35]C(=O)C2C=CC([N+]([O-])=O)=CC=2)=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O>[CH2:8]([O:15][C:16]1[CH:17]=[CH:18][C:19]([C@H:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[CH2:24][C@H:23]2[OH:35])=[CH:20][CH:21]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 118207427HCID 118207427, compound

Product 1

HCID 96930706HCID 96930706, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a suspension of KOH (5.06 g, 90 mmol), water (60 ml) and tetrahydrofuran (200 ml) was added tert-butyl 4-(4-(benzyloxy)phenyl)-3-((4-nitrobenzoyl)oxy)piperidine-1-carboxylate (6 g, 11.3 mmol) and the reaction mixture was stirred at room temperature overnight. It was then diluted with 200 mL water and extracted twice with 200 mL ethyl acetate. The organic layer was washed with 1.5 N HCl solution and was then dried over Na2SO4, filtered, and evaporated to dryness. The crude product 4 g, (±)-rel-(3S,4R)-tert-butyl 4-(4-(benzyloxy)phenyl)-3-hydroxypiperidine-1-carboxylate), was used in the next step without further purification. LCMS (method F) RT 2.44 min (95% AP), m/z 382 (M−H) (negative mode); 1H NMR (300 MHz, DMSO-d6) δ ppm 7.29-7.44 (m, 5H), 7.71 (d, J=8.4, 2H), 6.91 (d, J=8.4, 2H), 5.06 (s, 2H), 4.45 (br s, 1H), 3.80-4.20 (m, 2H), 3.70 (br s, 1H), 2.60-3.05 (m, 3H), 1.95-2.20 (m, 1H), 1.35 (s, 9H).

Workup

  1. extractionextracted twice with 200 mL ethyl acetate
  2. washThe organic layer was washed with 1.5 N HCl solution
  3. dry with materialwas then dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude product 4 g, (±)-rel-(3S,4R)-tert-butyl 4-(4-(benzyloxy)phenyl)-3-hydroxypiperidine-1-carboxylate), was used in the next step without further purification
  7. customLCMS (method F) RT 2.44 min (95% AP), m/z 382 (M−H) (negative mode)

Sources & evidence

ORD record
ord-f86dfba0175f4f93883c86b13b5d9e88
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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