Acetic Acid → HCID 59258500, compound

HRID 641189Notes

Reaction equation

HRID 641189 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.O=[C:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[O:12]=[C:10]1[NH:9][C:8]2[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=2[C:4]2([CH2:3][CH2:2][N:1]([CH:18]3[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]3)[CH2:6][CH2:5]2)[O:11]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 13050639Spiro[3,1-benzoxazine-4,4'-piperidin]-2(1H)-one

Product 1

HCID 59258500HCID 59258500, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Spiro[4H-3,1-benzoxazine-4,4′-piperidin]-2(1H)-one (A4) (410 mg, 1.88 mmol) was dissolved in anhydrous 1,2-dichloroethane (10 mL) and treated with tert-butyl 4-oxopiperidine-1-carboxylate (via) (562 mg, 2.82 mmol), glacial acetic acid (226 mg, 3.76 mmol) and sodium triacetoxyborohydride (797 mg, 3.76 mmol). The reaction was stirred under nitrogen at room temperature for 72 hours. The reaction was concentrated under reduced pressure and the residue partitioned between 1.0 N HCl (50 mL) and diethyl ether (25 mL). The aqueous layer was separated and washed with diethyl ether (2×25 mL), basified with 1.0 N NaOH (aq) and extracted with dichloromethane (3×50 mL). The pooled extracts were washed with saturated brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to afford tert-butyl 4-(2-oxo-1,2-dihydrospiro[benzo[d][1,3]oxazine-4,4′-piperidine]-1′-yl)piperidine-1-carboxylate (vib) as a crystalline white solid. LC/MS m/z 402.2 [M+H]+, retention time 1.84 min (RP-C18, 10-99% CH3CN/0.05% TFA).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. customthe residue partitioned between 1.0 N HCl (50 mL) and diethyl ether (25 mL)
  3. customThe aqueous layer was separated
  4. washwashed with diethyl ether (2×25 mL)
  5. extractionextracted with dichloromethane (3×50 mL)
  6. washThe pooled extracts were washed with saturated brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-33e2f263b6264953af99f732aa6da690
Source dataset
uspto-grants-2010_04
Patent number
US07696201B2

Reaction notes

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