Hydroxylamine → HCID 86680657, compound

HRID 1615416Notes

Reaction equation

HRID 1615416 reaction equation
[NH2:1][OH:2].[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]2[CH2:16][O:15][CH2:14][CH2:13][N:12]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:7][CH:6]=1)=O>C(O)C>[OH:2][N:1]=[CH:3][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]2[CH2:16][O:15][CH2:14][CH2:13][N:12]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 86680656HCID 86680656, compound

Product 1

HCID 86680657HCID 86680657, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine (2.513 mL of 50% w/v, 38.04 mmol) was added to a stirred solution of tert-butyl (3R)-3-(4-formylphenyl)morpholine-4-carboxylate 11 (5.54 g, 19.02 mmol) in ethanol (29.66 mL) and the resulting mixture stirred at rt for 1 h. The reaction mixture was concentrated in vacuo and then redissolved in EtOAc (50 mL) and sequentially washed with water (2×20 mL) and brine (1×20 mL), dried over MgSO4, filtered and concentrated in vacuo to leave product as a white foam (5.57 g, 96% yield); 1H NMR (400.0 MHz, DMSO) d 1.39 (9H, s), 3.08 (1H, m), 3.49 (1H, m), 3.69-3.83 (4H, m), 4.28 (1H, m), 4.98 (1H, s), 7.36 (2H, m), 7.58 (2H, m), 8.13 (1H, s) and 11.23 (1H, s) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionredissolved in EtOAc (50 mL)
  3. washsequentially washed with water (2×20 mL) and brine (1×20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-335c791825594dd682b9f777cd39fd3f
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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