Hydrochloric Acid → (2R,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-{2-(5-hydroxymethylimidazol-1-yl)ethyl}pyrrolidine

HRID 975702Notes

Reaction equation

HRID 975702 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH2:9][C@H:8]1[CH2:20][CH2:21][N:22]1[C:26]([CH:27]=[O:28])=[CH:25][N:24]=[CH:23]1)=[O:6])[CH:2]=[CH2:3].[BH4-].[Na+].Cl>O1CCCC1.CO>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si:13]([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:15])[CH3:14])[CH2:9][C@H:8]1[CH2:20][CH2:21][N:22]1[C:26]([CH2:27][OH:28])=[CH:25][N:24]=[CH:23]1)=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 54006383(2R,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-{2-(5-formylimidazol-1-yl)ethyl}pyrrolidine

Product 1

HCID 54006707(2R,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-{2-(5-hydroxymethylimidazol-1-yl)ethyl}pyrrolidineYield 80.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-{2-(5-formylimidazol-1-yl)ethyl}pyrrolidine (12.65 g) in a mixture of tetrahydrofuran (60 ml) and methanol (60 ml) was portionwise added sodium borohydride (1.17 g) with stirring under ice-cooling. The mixture was stirred at the same temperature for 1 hour. The reaction mixture was adjusted to pH 8 with 6N hydrochloric acid at the same condition. The resulting precipitates were filtered off and the filtrate was evaporated in vacuo to give a residue. The residue was chromatographed on silica gel (250 g) eluting with a mixture of chloroform and methanol (9:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2R,4R)-1-allyloxycarbonyl-4-t-butyldimethylsilyloxy-2-{2-(5-hydroxymethylimidazol-1-yl)ethyl}pyrrolidine (10.23 g).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 1 hour
  3. customThe resulting precipitates
  4. filtrationwere filtered off
  5. customthe filtrate was evaporated in vacuo
  6. customto give a residue
  7. customThe residue was chromatographed on silica gel (250 g)
  8. washeluting with a mixture of chloroform and methanol (9:1, V/V)
  9. additionThe fractions containing the desired compound
  10. customwere collected
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-75eb887a6351487abf025501235eaf7f
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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