1-Naphthaldehyde → (S)-1,1-diethoxy-N-(naphthalen-1-ylmethyl)propan-2-amine
Reaction equation
[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C@@H:5]([NH2:7])[CH3:6])[CH3:2].[C:11]1([CH:21]=O)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:3][CH:4]([O:8][CH2:9][CH3:10])[C@@H:5]([NH:7][CH2:21][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)[CH3:6])[CH3:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (S)-1,1-diethoxypropan-2-amine (Compound XVIII-1) (682 mg, 3.55 mmol) in tetrahydrofuran (2 ml) was added 1-naphthaldehyde (554 mg, 3.55 mmol) and the mixture was stirred at room temperature for 0.5 hr. The reaction mixture was diluted with tetrahydrofuran (3 ml) and sodium triacetoxyborohydride (829 mg, 3.91 mmol) was added and the mixture was stirred at room temperature for 18 hr. The reaction mixture was diluted with ethyl acetate (50 ml) and washed with saturated aqueous sodium bicarbonate (50 ml) twice, water (50 ml) twice and brine (50 ml) twice. The organic layer was dried over magnesium sulfate and filtered and the filtrate was concentrated in vacuo to obtain the title compound (685 mg, 67.1%).
Workup
- additionwas added
- stirringthe mixture was stirred at room temperature for 18 hr
- washwashed with saturated aqueous sodium bicarbonate (50 ml) twice
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationthe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-5d25f412261b42f9996e61e6279297e9
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691819B2
Reaction notes
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