(S)-5-(2-azido-ethyl)-2,2,4,4-tetramethyl-[1,3]dioxolane → 2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethylamine

HRID 1807062Notes

Reaction equation

HRID 1807062 reaction equation
[N:1]([CH2:4][CH2:5][C@@H:6]1[O:10][C:9]([CH3:12])([CH3:11])[O:8][C:7]1([CH3:14])[CH3:13])=[N+]=[N-]>C(OCC)(=O)C.O=[Pt]=O>[CH3:11][C:9]1([CH3:12])[O:10][C@@H:6]([CH2:5][CH2:4][NH2:1])[C:7]([CH3:14])([CH3:13])[O:8]1

Participants

4

Reactant 1

HCID 86640454(S)-5-(2-azido-ethyl)-2,2,4,4-tetramethyl-[1,3]dioxolane

Product 1

HCID 592495672-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethylamineYield 94%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Step I A suspension of (S)-5-(2-azido-ethyl)-2,2,4,4-tetramethyl-[1,3]dioxolane (1.6 g, 8 mmol) and PtO2 (0.32 g) in ethyl acetate (15 mL) was vigorously shaken in a Parr under atmosphere of H2 (50 psi) for 18 h. The mixture was filtered through a short pad of celite. The filtrate was concentrated to give 2-((S)-2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-ethylamine as a colorless oil (1.3 g, 94%).

Workup

  1. filtrationThe mixture was filtered through a short pad of celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-74889d72a36a41b1b6a2c0343ee84213
Source dataset
uspto-grants-2013_01
Patent number
US08354444B2

Reaction notes

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