Hydrochloric Acid → HCID 57171953, compound

HRID 1586748Notes

Reaction equation

HRID 1586748 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10](C(C)(C)C)[CH2:9][C@:8]1(O[SiH](C)C)[CH2:16][N:17]1[C:24]2[N:20]([N:21]=[CH:22][CH:23]=2)[CH:19]=[CH:18]1)=[O:6])[CH:2]=[CH2:3].Cl.C[O-:31].[Na+]>CO>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:31])[CH2:9][C@H:8]1[CH2:16][N:17]1[C:24]2[N:20]([N:21]=[CH:22][CH:23]=2)[CH:19]=[CH:18]1)=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 131717960HCID 131717960, compound

Product 1

HCID 57171953HCID 57171953, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of (2S,4R)-1-allyloxycarbonyl-4-tertbutyldimethylsilyloxy-2-(imidazo[1,2-b]pyrazol-1-yl)methylpyrrolidine (4.23 g) and conc. hydrochloric acid (2.61 ml) in methanol (40 ml) was stirred at ambient temperature for 5 hours. The reaction mixture was adjusted to pH 8-9 with 28% sodium methoxide in methanol solution and the mixture was concentrated in vacuo. The resulting residue was chromatographed on silica gel (100 g) eluting with a mixture of dichloromethane and acetone (2:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-1-allyloxycarbonyl-4-hydroxy-2-(imidazo [1,2-b]pyrazol-1-yl)methylpyrrolidine (3.18 g).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe resulting residue was chromatographed on silica gel (100 g)
  3. washeluting with a mixture of dichloromethane and acetone (2:1, V/V)
  4. additionThe fractions containing the desired compound
  5. customwere collected
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-17ce61d609e841fb9a8888650358ff49
Source dataset
uspto-grants-1993_06
Patent number
US05215983

Reaction notes

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