Triethylamine → 3-(4-{ethyl-[(S)-2-(4-methylsulfanyl-phenyl)-1-methylethyl]amino}butyl)-[1,3]oxazinan-2-one

HRID 900662Notes

Reaction equation

HRID 900662 reaction equation
Cl.[CH2:2]([NH:4][C@@H:5]([CH3:15])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[CH:9][CH:8]=1)[CH3:3].C(N(CC)CC)C.[O:23]=[C:24]1[N:29]([CH2:30][CH2:31][CH2:32][CH:33]=O)[CH2:28][CH2:27][CH2:26][O:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:2]([N:4]([C@@H:5]([CH3:15])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([S:13][CH3:14])=[CH:11][CH:12]=1)[CH2:33][CH2:32][CH2:31][CH2:30][N:29]1[CH2:28][CH2:27][CH2:26][O:25][C:24]1=[O:23])[CH3:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 159226964-(2-Oxo-[1,3]oxazinan-3-yl)butyraldehydeHCID 69223599ethyl-[(S)-2-(4-methylsulfanylphenyl)-1-methylethyl]-amine hydrochloride

Product 1

HCID 692253143-(4-{ethyl-[(S)-2-(4-methylsulfanyl-phenyl)-1-methylethyl]amino}butyl)-[1,3]oxazinan-2-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of ethyl-[(S)-2-(4-methylsulfanylphenyl)-1-methylethyl]-amine hydrochloride (0.25 g, 1 mmole) in 1,2-dichloroethane (10 mL) was added triethylamine (0.2 mL, 1.5 mmole). To this mixture was added 4-(2-oxo-[1,3]oxazinan-3-yl)butyraldehyde (0.18 g, 1.05 mmole) and sodium triacetoxyborohydride (0.32 g, 1.5 mmole). The reaction mixture was stirred at room temperature for 15 hours, concentrated, and the residue was partitioned between 5% sodium hydroxide (5 mL) and diethyl ether (20 mL). The organic phase was dried (magnesium sulfate) and concentrated to give 3-(4-{ethyl-[(S)-2-(4-methylsulfanyl-phenyl)-1-methylethyl]amino}butyl)-[1,3]oxazinan-2-one, (0.33 g,) as a viscous oil.

Workup

  1. concentrationconcentrated
  2. customthe residue was partitioned between 5% sodium hydroxide (5 mL) and diethyl ether (20 mL)
  3. dry with materialThe organic phase was dried (magnesium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0acd7275704f4193848be65090196a90
Source dataset
uspto-grants-2008_04
Patent number
US07361648B2

Reaction notes

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