3-Methylbutanal → HCID 25059926, compound

HRID 641188Notes

Reaction equation

HRID 641188 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([O:11][C:10](=[O:12])[NH:9][C:8]3[CH:13]=[CH:14][CH:15]=[CH:16][C:7]2=3)[CH2:3][CH2:2]1.[CH3:17][CH:18]([CH3:22])[CH2:19][CH:20]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:20]([N:1]1[CH2:2][CH2:3][C:4]2([O:11][C:10](=[O:12])[NH:9][C:8]3[CH:13]=[CH:14][CH:15]=[CH:16][C:7]2=3)[CH2:5][CH2:6]1)[CH2:19][CH:18]([CH3:22])[CH3:17]

Participants

5

Reactant 3

HCID 115523-MethylbutanalHCID 5049666Sodium triacetoxyborohydrideHCID 13050639Spiro[3,1-benzoxazine-4,4'-piperidin]-2(1H)-one

Product 1

HCID 25059926HCID 25059926, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Spiro[4H-3,1-benzoxazine-4,4′-piperidin]-2(1H)-one (A4) (22 mg, 0.10 mmol) was dissolved in anhydrous 1,2-dichloroethane (750 μL) in a scintillation vial and treated with 3-methylbutanal (va) (9 mg, 0.10 mmol), followed by sodium triacetoxyborohydride (30 mg, 0.14 mmol). The reaction was stirred at room temperature for 1 hour, then quenched with methanol (500 μL) and stirred at room temperature for an additional 30 minutes. The reaction was filtered (Whatman 0.45 μm PTFE) and subjected to reverse-phase HPLC purification [2-99% CH3CN gradient over 13 min with 0.1% TFA (aq), 35 mL/min, 1.0 mL injected] to provide 1′-isopentylspiro[benzo[d][1,3]oxazine-4,4′-piperidin]-2(1H)-one (compound no. 76). LC/MS m/z 289.0 [M+H]+, retention time 1.55 min (RP-C18, 10-99% CH3CN/0.05% TFA).

Workup

  1. customquenched with methanol (500 μL)
  2. stirringstirred at room temperature for an additional 30 minutes
  3. filtrationThe reaction was filtered (Whatman 0.45 μm PTFE)
  4. customsubjected to reverse-phase HPLC purification [2-99% CH3CN gradient over 13 min with 0.1% TFA (aq), 35 mL/min, 1.0 mL injected]

Sources & evidence

ORD record
ord-1d5fc00ce3644564b6128e46aec19c76
Source dataset
uspto-grants-2010_04
Patent number
US07696201B2

Reaction notes

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