Potassium Bicarbonate → tert-Butyl ((1S,3S)-3-hydroxycyclopentyl)carbamate

HRID 1420304Notes

Reaction equation

HRID 1420304 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([O:13]C=O)[CH2:9]1)([CH3:4])[CH3:3].C(=O)([O-])O.[K+]>CO.O.C(OCC)(=O)C>[CH3:4][C:2]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)([CH3:1])[CH3:3]

Participants

6

Reactant 2

HCID 516893Potassium BicarbonateHCID 86754023(1S,3S)-3-[(tert-Butoxycarbonyl)amino]cyclopentyl formate

Product 1

HCID 21637082tert-Butyl ((1S,3S)-3-hydroxycyclopentyl)carbamateYield 52.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (1S-trans)-[3-(formyloxy)cyclopentyl]carbamic acid 1,1-dimethylethyl ester (0.081 g, 0.35 mmol) in methanol (3 ml) was treated with a slurry of potassium hydrogen carbonate (0.707 g, 7.06 mmol) in water (1.5 ml) and stirred at room temperature for 2 h. The mixture was then diluted with water (20 ml) and ethyl acetate (20 ml) and the aqueous phase was extracted with ethyl acetate (2×20 ml). The combined organic phase was dried (MgSO4) and evaporated to leave a solid which was purified by column chromatography on flash silica eluting with 30-40% ethyl acetate in cyclohexane to give the title compound (0.037 g) from diisopropyl ether m.p. 83°-85° C., [α]D 0.0° (CHCl3 c=0.55%).

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate (2×20 ml)
  2. dry with materialThe combined organic phase was dried (MgSO4)
  3. customevaporated
  4. customto leave a solid which
  5. customwas purified by column chromatography on flash silica eluting with 30-40% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-67e185ffc50e4ea7bfde760c38d89529
Source dataset
uspto-grants-1999_03
Patent number
US05889178

Reaction notes

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