Tetrahydrofuran → HCID 178453956, compound

HRID 2391004Notes

Reaction equation

HRID 2391004 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](OC)=[O:16])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>C(O)C>[OH:16][CH2:15][C@H:12]1[CH2:11][CH2:10][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 178501239HCID 178501239, compound

Product 1

HCID 178453956HCID 178453956, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

Methyl trans-4-(tert-butoxycarbonylamino)cyclohexanecarboxylate (55.5 g, 216 mmol) is suspended in ethanol (900 mL) and THF (100 mL) and the mixture is cooled to 5° C. Granular calcium chloride (47.9 g, 431 mmol) is added portionwise to give a milky suspension. Sodium borohydride (32.6 g, 863 mmol) is added portionwise over 25 mins at 5° C. The reaction mixture (white emulsion) is stirred at 5° C. for 1 hour, the water bath is removed and then the reaction mixture is allowed to warm to room temperature and stirred at room temperature overnight. The reaction mixture is cooled to 10° C. and 5% potassium carbonate (200 mL) is added dropwise until the pH of the solution is pH 11. A colourless precipitate formed which is filtered off. The solid is stirred with ethyl acetate (2000 mL) and water (500 mL). The organic layer is separated and washed with 0.5M HCl (200 mL), then washed with water (2×200 mL) and saturated brine (100 mL). The organic solution is dried over anhydrous MgSO4, filtered and evaporated to give a white solid The solid is dried under high vacuum overnight to constant weight; [MH+ 230].

Workup

  1. customto give a milky suspension
  2. customthe water bath is removed
  3. temperatureto warm to room temperature
  4. stirringstirred at room temperature overnight
  5. temperatureThe reaction mixture is cooled to 10° C.
  6. addition5% potassium carbonate (200 mL) is added dropwise until the pH of the solution
  7. customA colourless precipitate formed which
  8. filtrationis filtered off
  9. stirringThe solid is stirred with ethyl acetate (2000 mL) and water (500 mL)
  10. customThe organic layer is separated
  11. washwashed with 0.5M HCl (200 mL)
  12. washwashed with water (2×200 mL) and saturated brine (100 mL)
  13. dry with materialThe organic solution is dried over anhydrous MgSO4
  14. filtrationfiltered
  15. customevaporated
  16. customto give a white solid The solid
  17. customis dried under high vacuum overnight to constant weight

Sources & evidence

ORD record
ord-16faed59ed5e44279a8071b91fb9bdd9
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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