Acetic Acid → HCID 124518668, compound

HRID 2200380Notes

Reaction equation

HRID 2200380 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][C@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[BH4-].[Na+].C(O)(=O)C>CO>[OH:1][CH:2]1[CH2:6][CH2:5][C@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH2:3]1.[OH:1][C@@H:2]1[CH2:6][CH2:5][C@H:4]([C:7]([O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:8])[CH2:3]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 70906909HCID 70906909, compound

Product 2

HCID 124518668HCID 124518668, compoundYield 158.6%HCID 131735707HCID 131735707, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-benzyl 3-oxocyclopentanecarboxylate (2 g, 9.16 mmol) in methanol (40 ml) was added sodium borohydride (0.35 g, 9.16 mmol) in portion wise manner at 0° C. and the reaction was allowed to stir at 0° C. for 20 min. Upon completion, acetic acid (0.57 ml, 10.08 mmol) was added to the reaction mixture and stirring was continued for 5 min. Methanol was removed under reduced pressure and to the residue was added water (50 ml). The organic mass was extracted using ethyl acetate (2×50 ml). Combined organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain a crude compound, which was purified by column chromatography over silica gel using ethyl acetate in hexane as eluents to obtain (1S)-benzyl 3-hydroxycyclopentanecarboxylate as a diastereomeric mixture (75:25) of title compound (1.6 g, 79%).

Workup

  1. stirringstirring
  2. waitwas continued for 5 min
  3. customMethanol was removed under reduced pressure and to the residue
  4. additionwas added water (50 ml)
  5. extractionThe organic mass was extracted
  6. dry with materialCombined organic layer was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto obtain a crude compound, which
  9. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-35520150255e4089a7c62486433fa747
Source dataset
uspto-grants-2016_06
Patent number
US09359367B2

Reaction notes

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