Ammonium Hydroxide → HCID 66813614, compound

HRID 1944780Notes

Reaction equation

HRID 1944780 reaction equation
O[N:2]=[CH:3][C@@H:4]([N:6]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]2[N:29]([C:30]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[N:28]=[N:27][N:26]=2)=[CH:15][CH:14]=1)[C:7](=[O:11])[CH2:8][CH2:9][CH3:10])[CH3:5].C([BH3-])#N.[Na+].C([O-])(=O)C.[NH4+].[OH-].[NH4+]>[Cl-].[Ti+3].[Cl-].[Cl-].CO>[NH2:2][CH2:3][C@@H:4]([N:6]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]2[N:29]([C:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[N:28]=[N:27][N:26]=2)=[CH:17][CH:18]=1)[C:7](=[O:11])[CH2:8][CH2:9][CH3:10])[CH3:5]

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 86622010HCID 86622010, compound

Product 1

HCID 66813614HCID 66813614, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 10313229titanium(III) trichlorideCatalystHCID 887MethanolSolvent

Procedure

A solution of intermediate (5d) (105 mg, 0.2 mmol), sodium cyanoborohydride (47 mg, 0.7 mmol), ammonium acetate (28 mg, 0.4 mmol), and MeOH (6.0 mL) was cooled to 0° C. After 15 minutes, titanium (III) chloride (83 mg, 0.5 mmol) was added. After 10 minutes, ammonium hydroxide (1 mL) was added and the mixture was stirred at room temperature for 5 minutes. The mixture was filtered through Celite®, rinsing with MeOH, and the filtrate was concentrated in vacuo to yield a white solid. The solid was extracted with DCM and water. The combined organic extracts were washed with saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated in vacuo to afford intermediate (5e) (95 mg), which was used directly in the next step.

Workup

  1. waitAfter 10 minutes
  2. filtrationThe mixture was filtered through Celite®
  3. washrinsing with MeOH
  4. concentrationthe filtrate was concentrated in vacuo
  5. customto yield a white solid
  6. extractionThe solid was extracted with DCM and water
  7. washThe combined organic extracts were washed with saturated aqueous NaCl
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1fd8810c5a5544f4808564baac434d54
Source dataset
uspto-grants-2013_03
Patent number
US08394846B2

Reaction notes

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