1,3-Dibromopropane → (1-Phenylcyclobutyl)methanamine

HRID 845118Notes

Reaction equation

HRID 845118 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:11][CH2:12][CH2:13]Br.[CH:15]1[N:20]=[C:19](Cl)[C:18]2[N:22]=[CH:23][N:24]([C@@H:25]3[O:29][C@H:28]([CH2:30][OH:31])[C@@H:27]([OH:32])[C@H:26]3[OH:33])[C:17]=2[N:16]=1>>[C:1]1([C:7]2([CH2:8][NH2:9])[CH2:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([C:7]2([CH2:8][NH:9][C:19]3[C:18]4[N:22]=[CH:23][N:24]([C:17]=4[N:16]=[CH:15][N:20]=3)[C@@H:25]3[O:29][C@H:28]([CH2:30][OH:31])[C@@H:27]([OH:32])[C@H:26]3[OH:33])[CH2:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 8794PhenylacetonitrileHCID 930036-Chloropurine riboside

Product 2

HCID 15611176(1-Phenylcyclobutyl)methanamineYield 62%HCID 15611197N6-((1-phenylcyclobutyl)methyl)adenosineYield 58.3%

Procedure

(1-Phenylcyclobutyl)methylamine is prepared from phenylacetonitrile (2.93 g, 25 mmol) and 1,3-dibromopropane (7.57 g, 37.5 mmol) as described in Example 1 in 62% yield. The above amine (1.61 g, 10 mmol) is reacted with 6-chloropurine riboside (2.87 g, 10 mmol) as described in Example 1. As the compound did not crystallize it is purified by removal of the solvent under reduced pressure, followed by dissolving the residual gum in ethyl acetate (50 mL) and washing it with water (2×25 mL) and saturated brine (25 mL) and drying (MgSO4). The solvent is removed under reduced pressure and the residual gum is subjected to flash chromatography on silica gel, eluting with 5% CH3OH in CHCl3. N6-((1-phenylcyclobutyl)methyl)adenosine (2.40 g, 58%) is obtained as a white solid foam m.p. 95°-118° C. Found: C, 61.21; H, 6.23; N, 17.24%. C21H25N5O4 calculated requires: C, 61.31; H, 6.08; N, 17.03%.

Workup

  1. customAs the compound did not crystallize it
  2. customis purified by removal of the solvent under reduced pressure
  3. dissolutionby dissolving the residual gum in ethyl acetate (50 mL)
  4. washwashing it with water (2×25 mL) and saturated brine (25 mL)
  5. dry with materialdrying (MgSO4)
  6. customThe solvent is removed under reduced pressure
  7. washeluting with 5% CH3OH in CHCl3

Sources & evidence

ORD record
ord-37c3bb4e7915473886ad27f7b78f5174
Source dataset
uspto-grants-1988_07
Patent number
US04755594

Reaction notes

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