Ethyl Acetate → [4-((S)-3-Hydroxy-cyclopentyl)-phenyl]-carbamic acid benzyl ester

HRID 1027401Notes

Reaction equation

HRID 1027401 reaction equation
[CH2:1]([O:8][C:9](=[O:23])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C@H:17]2[CH2:21][CH2:20][C:19](=[O:22])[CH2:18]2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOC(C)=O.[BH4-].[Na+]>CCO.CCCCCCC>[CH2:1]([O:8][C:9](=[O:23])[NH:10][C:11]1[CH:12]=[CH:13][C:14]([C@H:17]2[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]2)=[CH:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8857Ethyl Acetate2×HCID 4311764Sodium borohydrideHCID 67479216[4-((S)-3-Oxo-cyclopentyl)-phenyl]-carbamic acid benzyl ester

Product 1

HCID 67479260[4-((S)-3-Hydroxy-cyclopentyl)-phenyl]-carbamic acid benzyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8900HeptaneSolvent

Procedure

[4-((S)-3-Oxo-cyclopentyl)-phenyl]-carbamic acid benzyl ester (150 mg, 0.5 mmol) was dissolved in EtOH (1 mL) and EtOAc (0.1 mL) to form a clear solution. To this solution was added powder NaBH4 (50 mg) with stirring. The reaction was judged to be complete by TLC (30% EtOAc in heptane). The reaction was quenched by EtOAc (2 mL) and NaHCO3 aq. solution (2 mL). The two layers were separated and the aqueous layer was extracted with EtOAc (2×2 mL). The combined extracts were washed with NaHCO3 aq. (2 mL), brine (2 mL), and dried (K2CO3). The solution was filtered through a silica gel pad, eluted with EtOAc. The filtrate was concentrated to dryness to afford 155 mg (100%) of the title compound as a very white crystalline material. mp 99.0-100.6° C.

Workup

  1. customThe reaction was quenched by EtOAc (2 mL) and NaHCO3 aq. solution (2 mL)
  2. customThe two layers were separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×2 mL)
  4. washThe combined extracts were washed with NaHCO3 aq. (2 mL), brine (2 mL)
  5. dry with materialdried (K2CO3)
  6. filtrationThe solution was filtered through a silica gel pad
  7. washeluted with EtOAc
  8. concentrationThe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-e41da23dafc24a3bbd6b1d8c032a3b08
Source dataset
uspto-grants-2014_05
Patent number
US08735385B2

Reaction notes

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