(S)-4-(2-azido-ethyl)-2,2-dimethyl-[1,3]dioxolane → 2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethan-1-amine

HRID 909017Notes

Reaction equation

HRID 909017 reaction equation
[N:1]([CH2:4][CH2:5][C@H:6]1[CH2:10][O:9][C:8]([CH3:12])([CH3:11])[O:7]1)=[N+]=[N-]>C(OCC)(=O)C.O=[Pt]=O>[CH3:11][C:8]1([CH3:12])[O:7][C@@H:6]([CH2:5][CH2:4][NH2:1])[CH2:10][O:9]1

Participants

4

Reactant 1

HCID 11457936(S)-4-(2-azido-ethyl)-2,2-dimethyl-[1,3]dioxolane

Product 1

HCID 282937772-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethan-1-amineYield 88%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of (S)-4-(2-azido-ethyl)-2,2-dimethyl-[1,3]dioxolane as a yellow oil (18.7 g, 0.11 mol) and PtO2 (2.5 g) in ethyl acetate (100 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-dimethyl-[1,3]dioxolan-4-yl)-ethylamine as a colorless oil (14 g, 88%).

Workup

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

Sources & evidence

ORD record
ord-09430df2682e4d839ec868872fd8b91b
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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