HCID 70197618, compound → HCID 70198456, compound

HRID 456260Notes

Reaction equation

HRID 456260 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11](/[CH:13]=[CH:14]/[C:15](OC)=[O:16])[C@H:10]([NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Li+].[BH4-]>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][CH2:14][CH2:15][OH:16])[C@H:10]([NH:19][C:20](=[O:29])[O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 70197618HCID 70197618, compound

Product 1

HCID 70198456HCID 70198456, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 4148881Lithium borohydrideSolvent

Procedure

To a solution of benzyl (3S*,4R*)-1-(tert-butoxycarbonyl)-4-((E)-2-(methoxycarbonyl)vinyl)pyrrolidin-3-ylcarbamate (1.0 g, 2.47 mmol) in 100 mL THF, LiBH4 was added (0.2 g, 9.0 mmol) and the mixture was stirred at reflux for 9 hours. The mixture was quenched with H2O, extracted with EtOAc, the combined organic extracts were dried with Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with 10→50% EtOAc in hexane giving the title compound.

Workup

  1. temperatureat reflux for 9 hours
  2. customThe mixture was quenched with H2O
  3. extractionextracted with EtOAc
  4. dry with materialthe combined organic extracts were dried with Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel eluting with 10→50% EtOAc in hexane giving the title compound

Sources & evidence

ORD record
ord-b968560b0fd1449dac73847bb5df4cd9
Source dataset
uspto-grants-2013_07
Patent number
US08497383B2

Reaction notes

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