Hydroxyamine hydrochloride → HCID 58374179, compound

HRID 1948537Notes

Reaction equation

HRID 1948537 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:24])[C:10]([N:13]2[CH2:18][CH2:17][CH2:16][C@H:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:14]2)([CH3:12])[CH3:11])=[CH:5][CH:4]=1)#[N:2].[BH4-].[Na+].Cl.[NH2:28][OH:29].C(=O)(O)[O-].[Na+]>CO.CC(O)C.C(OCC)(=O)C>[OH:24][CH:9]([C:6]1[CH:7]=[CH:8][C:3](/[C:1](=[N:28]/[OH:29])/[NH2:2])=[CH:4][CH:5]=1)[C:10]([N:13]1[CH2:18][CH2:17][CH2:16][C@H:15]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:14]1)([CH3:12])[CH3:11]

Participants

8

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 68260699(S)-ethyl 1-(1-(4-cyanophenyl)-2-methyl-1-oxopropan-2-yl)piperidine-3-carboxylate

Product 1

HCID 58374179HCID 58374179, compoundYield 100.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a mixture of (S)-ethyl 1-(1-(4-cyanophenyl)-2-methyl-1-oxopropan-2-yl)piperidine-3-carboxylate (90 mg, 0.274 mmol) in MeOH (5 mL) was added sodium borohydride (15 mg, 0.396 mmol). After 1 hr, the reaction was quenched with water. The reaction mixture was diluted with ethyl acetate and washed with sat NaCl. The organic layer was dried MgSO4, filtered, and concentrated. To a mixture of hydroxylamine hydrochloride (38.1 mg, 0.548 mmol) and sodium bicarbonate (92 mg, 1.096 mmol) in 2-propanol (10 mL) was added the crude product from step one. The reaction mixture was heated at 75° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with H2O. The organic layer was dried MgSO4, filtered, and concentrated to yield 100 mg of (3S)-ethyl 1-(1-hydroxy-1-(4-((Z)—N′-hydroxycarbamimidoyl)phenyl)-2-methylpropan-2-yl)piperidine-3-carboxylate. MS (m+1)=364. HPLC Peak RT=0.27 minutes (Analytical Method B).

Workup

  1. customthe reaction was quenched with water
  2. additionThe reaction mixture was diluted with ethyl acetate
  3. washwashed
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washwashed with H2O
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dff7b0df98154f23a8fde924ce0afc0b
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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