Sodium borohydride → (1R,2S,3R,5R)-3-[(tert-Butoxycarbonyl)amino]5-(hydroxymethyl)cyclopentane-1,2-diyl dibenzoate

HRID 447596Notes

Reaction equation

HRID 447596 reaction equation
[C:1]([O:9][C@H:10]1[C@@H:15]([O:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:14]2[CH2:25][C@@H:11]1[C:12](=[O:33])[N:13]2[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[C:1]([O:9][C@@H:10]1[C@@H:11]([CH2:12][OH:33])[CH2:25][C@@H:14]([NH:13][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@@H:15]1[O:16][C:17](=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66798101tert-butyl (1R,4S,5R,6S)-5,6-bis(benzoyloxy)-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 59671317(1R,2S,3R,5R)-3-[(tert-Butoxycarbonyl)amino]5-(hydroxymethyl)cyclopentane-1,2-diyl dibenzoateYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (1R,4S,5R,6S)-5,6-bis(benzoyloxy)-3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate (2.09 g, 4.62 mmol) in MeOH (60.0 mL) was added sodium borohydride (700. mg, 18.5 mmol) at 0° C. and the reaction was allowed to warm to rt. After 1.5 h, the mixture was quenched with 1.00 N HCl solution (20.0 mL), and concentrated in vacuo. The aqueous layer was extracted with DCM (3×50 mL) and the combined organic layers were washed with H2O (100. mL), dried over MgSO4 and concentrated in vacuo. The residue was purified via silica gel chromatography eluting with a gradient of 20 to 60% EtOAc in hexanes to afford the title compound (1.50 g, 80%). LC/MS: Rt=1.95 min, ES+ 456 (FA standard).

Workup

  1. customthe mixture was quenched with 1.00 N HCl solution (20.0 mL)
  2. concentrationconcentrated in vacuo
  3. extractionThe aqueous layer was extracted with DCM (3×50 mL)
  4. washthe combined organic layers were washed with H2O (100. mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via silica gel chromatography
  8. washeluting with a gradient of 20 to 60% EtOAc in hexanes

Sources & evidence

ORD record
ord-c0800fb8c95b4a0b8048218d91cc8128
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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