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

HRID 480145Notes

Reaction equation

HRID 480145 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 was 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 CH2Cl2 (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 CH2Cl2 (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-0932d8ed86604c469d1f6fdf0d3b9db2
Source dataset
uspto-grants-2003_11
Patent number
US06649600B1

Reaction notes

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