Tert-Butylamine → 1,2-di-O-(n-hexadecyl)-3-O-[3-(1-hydroxy-2-t-butylaminoethyl)-benzyl]-glycerol

HRID 46509Notes

Reaction equation

HRID 46509 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([CH2:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([CH:46]2[O:48][CH2:47]2)[CH:41]=1)[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[C:49]([NH2:53])([CH3:52])([CH3:51])[CH3:50]>>[CH2:1]([O:17][CH2:18][CH:19]([CH2:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([CH:46]([OH:48])[CH2:47][NH:53][C:49]([CH3:52])([CH3:51])[CH3:50])[CH:41]=1)[O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 6385Tert-Butylamine2×HCID 234661101,2-Di-O-(n-hexadecyl)-3-O-[3-(1,2-epoxyethyl)benzyl]-glycerol

Product 1

HCID 203873961,2-di-O-(n-hexadecyl)-3-O-[3-(1-hydroxy-2-t-butylaminoethyl)-benzyl]-glycerolYield 27%

Conditions

Temperature
100 °C

Procedure

t-Butylamine (30 ml) and 1,2-di-O-(n-hexadecyl)-3-O-[3-(1,2-epoxyethyl)-benzyl]-glycerol (2.0 g, 2.97 mmol) were placed in a steel bomb and heated to 100° C. for 9 hours. After cooling the reaction mixture, t-butylamine was removed under reduced pressure and the resulting oil purified by silica gel chromatography, eluted with benzene/ethanol. The desired fractions were saturated with gaseous hydrochloric acid, concentrated under reduced pressure, and recrystallized from ethyl acetate to give pure 1,2-di-O-(n-hexadecyl)-3-O-[3-(1-hydroxy-2-t-butylaminoethyl)-benzyl]-glycerol (630 mg, 27%): mp 49°-51° C.; NMR (CDCl3) δ 1.47 [s, 9, --C(CH3)3 ].

Workup

  1. customwas removed under reduced pressure
  2. customthe resulting oil purified by silica gel chromatography
  3. washeluted with benzene/ethanol
  4. concentrationconcentrated under reduced pressure
  5. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-52cce78ddb654acb97484eba743edd3c
Source dataset
uspto-grants-1979_11
Patent number
US04173641

Reaction notes

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