Hydrochloric Acid → (1RS,2RS,3RS)-2-Carbomethoxy-3-hydroxy-tropane, hydrochloride

HRID 742320Notes

Reaction equation

HRID 742320 reaction equation
[C:1]([CH:5]1[C:11](=[O:12])[CH2:10][C@H:9]2[N:13]([CH3:14])[CH:6]1[CH2:7][CH2:8]2)([O:3][CH3:4])=[O:2].[BH4-].[Na+].[ClH:17]>CO.C(O)C>[ClH:17].[C:1]([CH:5]1[CH:11]([OH:12])[CH2:10][C@H:9]2[N:13]([CH3:14])[CH:6]1[CH2:7][CH2:8]2)([O:3][CH3:4])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 131718787(1RS,2RS)-2-Carbomethoxy-3-tropanone

Product 1

HCID 131718788(1RS,2RS,3RS)-2-Carbomethoxy-3-hydroxy-tropane, hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of (1RS,2RS)-2-carbomethoxy-3-tropanone (17 g, 85 mmol) in 750 ml methanol cooled to -35° C. was added sodium borohydride (17 g, 450 mmol) and the mixture was stirred for 4 hours. The cooled solution was quenched by slow addition of concentrated hydrochloric acid (40 ml) and the mixture was concentrated in vacuo. Water (400 ml) was added and the pH was adjusted to 3 by addition of concentrated hydrochloric acid. After having washed the water phase three times with diethyl ether pH was adjusted to 11 by addition of concentrated ammonium hydroxide and the water phase was extracted three times with methylene chloride. Concentration in vacuo yields an oil which was dissolved in ethanol and added cocncentrated hydrochloric acid followed by concentration in vacuo. Freeze drying the residue yielded the title compound as an amorphous product.

Workup

  1. customThe cooled solution was quenched by slow addition of concentrated hydrochloric acid (40 ml)
  2. concentrationthe mixture was concentrated in vacuo
  3. additionWater (400 ml) was added
  4. additionthe pH was adjusted to 3 by addition of concentrated hydrochloric acid
  5. washAfter having washed the water phase three times with diethyl ether
  6. additionpH was adjusted to 11 by addition of concentrated ammonium hydroxide
  7. extractionthe water phase was extracted three times with methylene chloride
  8. concentrationConcentration in vacuo
  9. customyields an oil which
  10. additionadded
  11. concentrationfollowed by concentration in vacuo
  12. customFreeze drying the residue

Sources & evidence

ORD record
ord-b20dd74ec64b44dda8f8a3c49c3f3c30
Source dataset
uspto-grants-1996_09
Patent number
US05554626

Reaction notes

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