Triethylamine → 2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethan-1-amine

HRID 1806843Notes

Reaction equation

HRID 1806843 reaction equation
O[CH2:2][CH2:3][C@@H:4]1[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5]1.CS(Cl)(=O)=O.C([N:18](CC)CC)C.[N-]=[N+]=[N-].[Na+]>ClCCl.CN(C)C=O.C(OCC)(=O)C.O=[Pt]=O>[CH3:9][C:6]1([CH3:10])[O:5][C@H:4]([CH2:3][CH2:2][NH2:18])[CH2:8][O:7]1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 11480522(4R)-4-(2-Hydroxyethyl)-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 282937752-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethan-1-amine

Reagents, catalysts & solvents 4

HCID 345198Adams' catalystCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Step A In a manner similar to the method described in Example 3a Step A to C, (4R)-(−)-4-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolane (Aldrich) (4.91 g, 33.6 mmol) was reacted with methanesulfonyl chloride (3.12 mL, 40.3 mmol) and triethylamine (9.34 mL, 67 mmol) in dichloromethane, then reacted with NaN3 (10.7 g, 0.16 mol) in N,N-dimethylformamide, then treated with PtO2 and H2 (50 psi) in ethyl acetate to give 2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethylamine as a brown oil (4.4 g, 90% for three steps).

Sources & evidence

ORD record
ord-0a422cad0a334c4ea1124acbdb87778e
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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