Ammonium Chloride → HCID 68706007, compound

HRID 732311Notes

Reaction equation

HRID 732311 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:12]2[O:11][CH:10]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][O:23][CH3:24])=[CH:17][CH:16]=3)[CH:9]3[CH2:25][C:26](=[O:28])[CH2:27][CH:8]3[C:7]=2[CH:6]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO.C1COCC1.CCOC(C)=O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:12]2[O:11][CH:10]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH2:22][O:23][CH3:24])=[CH:19][CH:20]=3)[CH:9]3[CH2:25][CH:26]([OH:28])[CH2:27][CH:8]3[C:7]=2[CH:6]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 68705549HCID 68705549, compound

Product 1

HCID 68706007HCID 68706007, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of cyclopentanon 23 (60 mg, 0.16 mmol) in 1 mL of MeOH and 0.5 mL of THF was added NaBH4 (15 mg, 0.40 mmol). After stirring for 2 hrs saturated aqueous ammonium chloride was added. The solution was diluted with EtOAc. The aqueous solution was extracted 2× with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated to give 60 mg (0.16 mmol, 100%) of alcohol 25. HRMS (ES+) calc for C22H30NO6: 404.2073, found: 404.2082 (M+NH4).

Workup

  1. additionwas added
  2. extractionThe aqueous solution was extracted 2× with EtOAc
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-076ddd87d3f842bdac1e9b4f355dc026
Source dataset
uspto-grants-2009_09
Patent number
US07585985B2

Reaction notes

Loading…