Sodium triacetoxyborohydride → tert-Butyl 2,2-dimethyl-5-((5-(5-(4-propylphenyl)-1,2,4-oxadiazol-3-yl)-3,4-dihydroquinolin-1(2H)-yl)methyl)-1,3-dioxan-5-ylcarbamate

HRID 710480Notes

Reaction equation

HRID 710480 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:16]=3[CH2:17][CH2:18][CH2:19][NH:20]4)[N:11]=2)=[CH:6][CH:5]=1)[CH2:2][CH3:3].[CH:25]([C:27]1([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[CH2:32][O:31][C:30]([CH3:34])([CH3:33])[O:29][CH2:28]1)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.CCOC(C)=O>[CH3:33][C:30]1([CH3:34])[O:29][CH2:28][C:27]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])([CH2:25][N:20]2[C:21]3[C:16](=[C:15]([C:12]4[N:11]=[C:10]([C:7]5[CH:6]=[CH:5][C:4]([CH2:1][CH2:2][CH3:3])=[CH:9][CH:8]=5)[O:14][N:13]=4)[CH:24]=[CH:23][CH:22]=3)[CH2:17][CH2:18][CH2:19]2)[CH2:32][O:31]1

Participants

6

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 24754730Tert-butyl (5-formyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamateHCID 667263485-(4-Propylphenyl)-3-(1,2,3,4-tetrahydroquinolin-5-yl)-1,2,4-oxadiazole

Product 1

HCID 86661812tert-Butyl 2,2-dimethyl-5-((5-(5-(4-propylphenyl)-1,2,4-oxadiazol-3-yl)-3,4-dihydroquinolin-1(2H)-yl)methyl)-1,3-dioxan-5-ylcarbamateYield 53.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of the product of Step D (0.0334 g; 0.1 mmol), tert-butyl 5-formyl-2,2-dimethyl-1,3-dioxan-5-ylcarbamate (3×0.03 g; 0.33 mmol) and NaBH(OAc)3 (3×0.07 g; 0.93 mmol) in 1,2-dichloroethane (1.5 ml) AcOH (3×0.01 ml) was added portion wise over a period of 3 days with stirring at room temperature. The mixture was then diluted to 15 ml with EtOAc, washed with 10% NaOH, H2O, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness under reduced pressure. The residue was purified by FCC (SiO2, hexane:EtOAc, 9:1), to give the title compound (0.03 g; 51%) as colourless foam. 1H-NMR (CDCl3) 0.95 (tr, 3H, J=7.4 Hz); 1.44 (m, 15H); 1.61-1.72 (m, 2H); 1.89-1.97 (m, 2H); 2.66 (tr, 2H, J=7.8 Hz); 3.06 (tr, 2H; J=6.5 Hz); 3.34 (tr, 2H, J=5.4 Hz); 3.77 (s, 2H); 3.95 (s, 4H); 4.7 (broad s, 1H); 7.02 (d, 1H, J=7.6 Hz); 7.14 (tr, 1H, J=7.6 Hz); 7.22-7.25 (m, 1H+CDCl3); 7.33 (d, 2H, J=8.3 Hz); 8.09 (d, 2H, J=8.3 Hz).

Workup

  1. additionwas added portion wise over a period of 3 days
  2. washwashed with 10% NaOH, H2O, brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. customfiltrate evaporated to dryness under reduced pressure
  6. customThe residue was purified by FCC (SiO2, hexane:EtOAc, 9:1)

Sources & evidence

ORD record
ord-3c4ff47190d44331835d3d4855822c5d
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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