Hydrochloric Acid → HCID 86680655, compound

HRID 1615414Notes

Reaction equation

HRID 1615414 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]2[CH2:16][O:15][CH2:14][CH2:13][N:12]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:7][CH:6]=1)=O.[BH4-].[Li+].Cl>C1COCC1.CCOC(C)=O>[OH:2][CH2:3][C:5]1[CH:6]=[CH:7][C:8]([C@@H:11]2[CH2:16][O:15][CH2:14][CH2:13][N:12]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydride2×HCID 86680654HCID 86680654, compound

Product 1

HCID 86680655HCID 86680655, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (3R)-3-(4-methoxycarbonylphenyl)morpholine-4-carboxylate 9 (6.91 g, 21.50 mmol) in THF (140 mL) was added lithium borohydride (1.873 g, 86.00 mmol) and the resulting mixture then heated under reflux overnight. Additional lithium borohydride (341 mg, 2 eq) was added and the reaction mixture heated under reflux for 2 h. The reaction mixture was cooled in an ice bath and then added ice-water, followed by 2M HCl (10 mL) and stirred until effervescence ceased then diluted with EtOAc (100 mL), mixed and the organic layer separated, washed sequentially with water (1×50 mL), brine (1×50 mL), dried over MgSO4, filtered and concentrated in vacuo to leave the product as a colourless viscous oil (6.0 g, 95% yield); 1H NMR (400.0 MHz, DMSO) d 1.40 (9H, s), 3.01 (1H, m), 3.49 (1H, m), 3.71-3.83 (3H, m), 4.27 (1H, m), 4.47 (2H, m), 4.96 (1H, s), 5.17 (1H, m) and 7.30 (4H, m) ppm.

Workup

  1. temperaturethe resulting mixture then heated
  2. temperatureunder reflux overnight
  3. temperaturethe reaction mixture heated
  4. temperatureunder reflux for 2 h
  5. temperatureThe reaction mixture was cooled in an ice bath
  6. additionmixed
  7. customthe organic layer separated
  8. washwashed sequentially with water (1×50 mL), brine (1×50 mL)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-800122b6ae514164a1ab23a608d45ca5
Source dataset
uspto-grants-2014_07
Patent number
US08765751B2

Reaction notes

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