Phosphate → HCID 53662183, compound

HRID 328751Notes

Reaction equation

HRID 328751 reaction equation
[C:1]1(=O)CCCC1.P([O-])([O-])([O-])=O.[BH4-].[Na+].[C:14]([O:17][CH:18]1[CH:22]([CH2:23][C:24]([OH:26])=[O:25])[CH:21]([C:27]([O:29][CH3:30])=[O:28])[CH:20]([OH:31])[CH2:19]1)(=[O:16])[CH3:15]>O.CO>[CH3:1][O:25][C:24](=[O:26])[CH2:23][CH:22]1[CH:18]([O:17][C:14](=[O:16])[CH3:15])[CH2:19][CH:20]([OH:31])[CH:21]1[C:27]([O:29][CH3:30])=[O:28]

Participants

7

Reactant 4

HCID 1061PhosphateHCID 8452CyclopentanoneHCID 4311764Sodium borohydrideHCID 21440260HCID 21440260, compound

Product 1

HCID 53662183HCID 53662183, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The cyclopentanone VI (8.6 g.), obtained according to the previous example, is dissolved in 50 ml. of methanol and added to 500 ml. of a phosphate buffer adjusted to a pH of 5.3. Then 20 ml. of an aqueous solution containing an excess of sodium borohydride (1.25 g.) is added at 5° C. After two hours at room temperature, 200 ml. of water is added to the reaction mixture which is then extracted several times with ethyl acetate. The combined organic layers are dried on MgSO4 and then evaporated to dryness giving 8.4 g. (98%) of crude methylester of 5-acetoxy-2-carbomethoxy-3-hydroxycyclopentaneacetic acid. This product examined by gas chromatography exhibits an 80% purity. The product which may be further purified by column chromatography has all the substituent groups with the desired orientation. The compound may not be distilled without decomposition. The principal absorption peaks in the N.M.R. spectrum in CDCl3 occur at the following frequencies expressed in δ units: 2.05 (3H, singlet), 3.65 (3H, singlet), 3.72 (3H, singlet), 4.30-4.70 (1H, multiplet, 5.18-5.43 (1H, multiplet).

Workup

  1. dissolutionis dissolved in 50 ml
  2. additionis added at 5° C
  3. extractionis then extracted several times with ethyl acetate
  4. customThe combined organic layers are dried on MgSO4
  5. customevaporated to dryness
  6. customgiving 8.4 g
  7. customThe product which may be further purified by column chromatography
  8. distillationThe compound may not be distilled without decomposition
  9. customThe principal absorption peaks in the N.M.R

Sources & evidence

ORD record
ord-ab87d89a3b1c4722826e06dad30d5bb7
Source dataset
uspto-grants-1977_04
Patent number
US04018797

Reaction notes

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