Sodium borohydride → tert-butyl (1R,3R,4S)-4-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-3-(hydroxymethyl)cyclohexylcarbamate

HRID 1171555Notes

Reaction equation

HRID 1171555 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]2[CH2:23][CH2:22][C@@H:21]3[CH2:24][C@H:18]2[C:19](=[O:32])[N:20]3[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:13]1=[O:33])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1.O>[C:28]([O:27][C:25](=[O:26])[NH:20][C@@H:21]1[CH2:22][CH2:23][C@H:17]([N:14]2[CH2:15][CH2:16][C@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[C:13]2=[O:33])[C@H:18]([CH2:19][OH:32])[CH2:24]1)([CH3:31])([CH3:29])[CH3:30]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 67182479HCID 67182479, compound

Product 1

HCID 68767819tert-butyl (1R,3R,4S)-4-((S)-3-benzyloxycarbonylamino-2-oxopyrrolidin-1-yl)-3-(hydroxymethyl)cyclohexylcarbamateYield 56.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R,2S,5R)-tert-butyl 2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-7-oxo-6-aza-bicyclo[3.2.1]octane-6-carboxylate (4.55 g, 9.94 mmol) in THF (50 mL) and water (50 mL) was added NaBH4, and the mixture was stirred for 5 h at rt. After quenching the reaction with sat. NaHCO3, the product was extracted with EtOAc (2×). The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo to give an oily residue, which crystallized upon tritulation with 4:6 EtOAc and hexane to provide pure ((1R,3R,4S)-4-((S)-3-(benzyloxycarbonyl)amino-2-oxopyrrolidin-1-yl)-3-(hydroxymethyl)cyclohexyl)carbamic acid tert-butyl ester (2.61 g).

Workup

  1. customAfter quenching
  2. customthe reaction with sat. NaHCO3
  3. extractionthe product was extracted with EtOAc (2×)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give an oily residue, which
  9. customcrystallized upon tritulation with 4:6 EtOAc and hexane

Sources & evidence

ORD record
ord-d1c08e3aedf941f0a409c6bf2216cd3d
Source dataset
uspto-grants-2010_11
Patent number
US07829571B2

Reaction notes

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