Hydroxylamine → HCID 58962277, compound

HRID 1365727Notes

Reaction equation

HRID 1365727 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]1([C:11]#[N:12])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[Na+].[I-].[NH2:15][OH:16].[C:17]([C:24]([O:26][CH2:27][CH3:28])=[O:25])#[C:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CCOC(C)=O>[CH2:22]([O:21][C:19](=[O:20])[CH2:18][C:17]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[O:16][N:15]2[CH2:2][CH2:3][CH2:4][C:5]3([CH2:10][CH2:9][O:8][CH2:7][CH2:6]3)[C:11]2=[N:12]1)[CH3:23]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 5238Sodium IodideHCID 69803Diethyl acetylenedicarboxylateHCID 57426433HCID 57426433, compound

Product 1

HCID 58962277HCID 58962277, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(3-chloropropyl)-tetrahydro-2H-pyran-4-carbonitrile (1.83 g, 9.75 mmol) and NaI (3.0 g, 20 mmol) was stirred at ambient temperature for 1 h. To this reaction mixture was added 50% aqueous hydroxylamine (1 mL, 10.87 mmol) and stirred for three-days at ambient temperature. To this was added diethyl acetylenedicarboxylate (1.6 mL, 10 mmol) and stirred for 1 h. Then, the reaction mixture was diluted with EtOAc (100 mL) washed with water (50 mL), brine (10 mL), dried (Na2SO4), filtered and concentrated to give yellow oil. Flash chromatography using 10-50% EtOAc/Hexanes afforded the title compound as pale yellow oil (0.627 g, 18%). 1H NMR (500 MHz, CDCl3) δ: HRMS (M+H) calcd for C17H27N2O5; found. 1H NMR (500 MHz, CDCl3) δ: 4.32-4.20 (2H, m), 4.14 (2H, q, J=7.0 Hz), 3.86 (1H, td, J=11.0, 2.7 Hz), 3.79-3.70 (3H, m), 3.52-3.46 (1H, m), 3.38-3.34 (1H, m), 3.26 (1H, d, JAB=16.2 Hz), 2.97 (1H, d, JAB=16.2 Hz), 2.06-1.89 (4H, m), 1.66-1.66 (2H, m), 1.60-1.53 (2H, m), 1.30 (3H, t, J=7.0 Hz), 1.24 (3H, t, J=7.0 Hz).

Workup

  1. stirringstirred for three-days at ambient temperature
  2. stirringstirred for 1 h
  3. washwashed with water (50 mL), brine (10 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give yellow oil

Sources & evidence

ORD record
ord-e3284250a5944e42b0b0f53937c7b4bf
Source dataset
uspto-grants-2011_02
Patent number
US07893055B2

Reaction notes

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