tert-Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamate → 2-Amino-2-((4-octylphenylamino)methyl)propane-1,3-diol

HRID 710280Notes

Reaction equation

HRID 710280 reaction equation
CC1(C)[O:7][CH2:6][C:5]([NH:24]C(=O)OC(C)(C)C)([CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][CH:11]=2)[CH2:4][O:3]1>FC(F)(F)C(O)=O.C(Cl)Cl.CO>[NH2:24][C:5]([CH2:8][NH:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:14][CH:15]=1)([CH2:6][OH:7])[CH2:4][OH:3]

Participants

5

Reactant 1

HCID 66726563tert-Butyl 2,2-dimethyl-5-((4-octylphenylamino)methyl)-1,3-dioxan-5-ylcarbamate

Product 1

HCID 461947402-Amino-2-((4-octylphenylamino)methyl)propane-1,3-diolYield 82.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of a product of Step A (0.32 g; 0.71 mmol) in 60% trifluoroacetic acid in CH2Cl2 (4 ml) was stirred for 15 min at room temperature then diluted to 6 ml with methanol (MeOH). The resulting mixture was evaporated to dryness under reduced pressure and the residue dried in vacuo for 1 h. This was purified by flash column chromatography (FCC) (SiO2; CH2Cl2 saturated with NH4OH:MeOH 95:5), to give pure title compound (0.18 g; 82%), as colourless solid. 1H-NMR (CDCl3) 0.86 (tr, 2H, J=6.96 Hz); 1.25 (m, 10H); 1.52 (m, 2H); 2.1-2.51 (broad m, 4H); 2.47 (tr, 2H, J=7.9 Hz); 3.1 (s, 2H); 3.55 (m, 4H); 4.05 (broad s, 1H); 6.6 (d, 2H, J=8.34 Hz); 6.96 (d, 2H, J=8.34 Hz).

Workup

  1. customThe resulting mixture was evaporated to dryness under reduced pressure
  2. customthe residue dried in vacuo for 1 h
  3. customThis was purified by flash column chromatography (FCC) (SiO2; CH2Cl2 saturated with NH4OH:MeOH 95:5)

Sources & evidence

ORD record
ord-12e0f1ee38b74d1d97d67e19c89a50cb
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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