2-Methyl-2-butene → HCID 178456483, compound

HRID 2105672Notes

Reaction equation

HRID 2105672 reaction equation
[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[NH:8][C:7]([C:14]34[CH2:21][CH2:20][C:17]([CH2:22][CH:23]=[O:24])([CH2:18][CH2:19]3)[CH2:16][CH2:15]4)=[N:6][C:5]=2[C:4](=[O:25])[N:3]1[CH2:26][CH2:27][CH3:28].CC(=CC)C.[O-:34]Cl=O.[Na+]>CC(O)(C)C>[O:1]=[C:2]1[N:10]([CH2:11][CH2:12][CH3:13])[C:9]2[NH:8][C:7]([C:14]34[CH2:19][CH2:18][C:17]([CH2:22][C:23]([OH:34])=[O:24])([CH2:20][CH2:21]3)[CH2:16][CH2:15]4)=[N:6][C:5]=2[C:4](=[O:25])[N:3]1[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 178456482HCID 178456482, compound

Product 1

HCID 178456483HCID 178456483, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of [4-(2,6-dioxo-1,3-dipropyl-2,3,6,9-tetrahydro-1H-purin-8-yl)-bicyclo[2.2.2]oct-1-yl]-acetaldehyde (170 mg, 0.440 mmol) in t-BuOH (10 ml) and 2-methyl-2-butene (10 eq, 4.4 mmol, 470 μL), cooled with the aid of an ice bath, was added NaClO2 (1.5 eq, 0.66 mmol). The resulting yellow solution as allowed to reach ambient temperature over a period of 14 h then concentrated in vacuo. The resulting oily residue was partitioned between water (10 ml) and CH2C (10 ml). The aqueous phase was acidified by the dropwise addition of concentrated HCl and the resulting precipitate was collected, washed with water and dried to afford 105 mg (59%) as a white powder. 1H NMR (400 MHz, CDCl3); d 0.91 (t, 3H), 0.93 (t, 3H), 1.63 (m, 2H), 1.77 (m, 2H; partially-obscured), 1.82 (m, 6H), 2.01 (m, 6H), 2.32 (s, 2H), 3.95 (m, 2H), 4.07 (m; 2H), 12.74 (s, 1H).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe resulting oily residue was partitioned between water (10 ml) and CH2C (10 ml)
  3. additionThe aqueous phase was acidified by the dropwise addition of concentrated HCl
  4. customthe resulting precipitate was collected
  5. washwashed with water
  6. customdried
  7. customto afford 105 mg (59%) as a white powder

Sources & evidence

ORD record
ord-a2723046819844df81183208e7537175
Source dataset
uspto-grants-2009_08
Patent number
US07579354B2

Reaction notes

Loading…