(2R)-3-Chloro-1,2-propanediol → (S)-2,3-Dihydroxy-N,N,N-trimethylpropan-1-aminium chloride

Reaction equation

C1(C)CCC(C(C)C)[CH:3]([N:10]([CH:21]2C(C(C)C)CCC(C)C2)[CH:11]2C(C(C)C)CCC(C)C2)C1.[Cl:32][CH2:33][C@H:34]([OH:37])[CH2:35][OH:36]>>[Cl-:32].[OH:37][C@H:34]([CH2:35][OH:36])[CH2:33][N+:10]([CH3:21])([CH3:11])[CH3:3]

Participants

Reactant 2

HCID 148793(2R)-3-Chloro-1,2-propanediol

HCID 53934826Trimenthylamine

Product 1

HCID 13668848(S)-2,3-Dihydroxy-N,N,N-trimethylpropan-1-aminium chloride

Procedure

There was added 80 ml of 30 w/v % aqueous solution of trimenthylamine to 20.00 g of (R)-3-chloro-1,2-propanediol (optical purity: 100% e.e., chemical purity: 99%). After stirring for 2 hours at room temperature, the reaction mixture was evaporated to dryness to give 30.40 g of (S)-2,3-dihydroxypropyltrimethylammonium chloride.

Workup

customthe reaction mixture was evaporated to dryness

Sources & evidence

ORD record: ord-d8e8d1af33f5483a98ebaa07d5a03368
Source dataset: uspto-grants-1989_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04814506

Reaction notes

Loading…