Dimethyl Sulfoxide → HCID 86599000, compound

HRID 1292977Notes

Reaction equation

HRID 1292977 reaction equation
[CH:1]1([CH2:7][C:8]([OH:21])([CH2:11][C:12]([CH3:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CS(C)=O>C(N(CC)CC)C>[CH:1]1([CH2:7][C:8]([OH:21])([CH2:11][C:12]([CH3:13])([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH3:20])[CH:9]=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 679Dimethyl SulfoxideHCID 69420884HCID 69420884, compound

Product 1

HCID 86599000HCID 86599000, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Analogously to Example 1, 160 mg of 2-cyclohexylmethyl-4-methyl-4-phenyl-1,2-pentanediol is reacted with 342 mg of pyridine-sulfur trioxide complex, 1.95 ml of DMSO and 0.39 ml of triethylamine to form 2-cyclohexylmethyl-2-hydroxy-4-methyl-4-phenylpentanal ('H-NMR (CDCl3); δ=0.90-1.60 (m, 10H), 1.30 (s, 3H), 1.41 (s, 3H), 1.76 (m, 2H), 1.95 (m, 1H), 2.20 (d, 1H), 2.35 (d, 1H), 2.97 (s, 1H), 7.20 (m, 1H), 7.30 (m, 4H), 8.76 (s, 1H)). The crude product is reacted with 137 mg of 5-aminoquinoline and 524 mg of sodium triacetoxy borohydride to form imine (180 mg; 'H-NMR (CDCl3); δ=0.90-1.90 (m, 18H), 2.25 (m, 1H), 2.80 (d, 1H), 3.00 (d, 1 H), 3.76 (t, 1H), 5.06 (d, 1H), 6.25 (d, 1H), 7.10-7.55 (m, 8H), 8.25 (d, 1H), 8.87 (dd, 1H); MS (ESI), 415). Reductive amination with 49 mg of sodium borohydride yields 130 mg of end product after column chromatography.

Sources & evidence

ORD record
ord-8decf5d0586641aaa0e2d25efc9755f6
Source dataset
uspto-grants-2007_07
Patent number
US07238707B2

Reaction notes

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