Ammonium Hydroxide → HCID 67354107, compound

HRID 1670828Notes

Reaction equation

HRID 1670828 reaction equation
C[O:2][C:3](=O)[CH:4]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][Si:15]([C:28]([CH3:31])([CH3:30])[CH3:29])([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)[CH2:5][C:6]#[N:7].[BH4-].[Na+].[OH-].[NH4+]>C1COCC1.O.O.O.O.O.O.O.[Co](Cl)Cl>[C:28]([Si:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[O:14][CH:11]1[CH2:10][CH2:9][N:8]([CH:4]2[CH2:5][CH2:6][NH:7][C:3]2=[O:2])[CH2:13][CH2:12]1)([CH3:30])([CH3:31])[CH3:29]

Participants

7

Reactant 3

HCID 14923Ammonium HydroxideHCID 4311764Sodium borohydrideHCID 67356080HCID 67356080, compound

Product 1

HCID 67354107HCID 67354107, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Treat a 0° C. mixture of 2-[4-(tert-butyl-diphenyl-silanyloxy)-piperidin-1-yl]-3-cyano-propionic acid methyl ester (3.32 g, 7.40 mmol) and cobalt (II) chloride hexahydrate (0.87 g, 3.65 mmol) in THF (60 mL) and water (30 mL) portion-wise with sodium borohydride (1.39 g, 36.7 mmol), warm to room temperature, and stir for 2 days under N2. Treat the reaction with 28% ammonium hydroxide (1 mL) and filter through hyflo. Remove the solvent from the filtrate in vacuo, dilute the residue with minimal water and brine, and extract three times with 3:1 chloroform:isopropanol. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and purify with a 0 to 10% methanol in CH2Cl2 gradient to afford 1.68 g (54%) of the titled product. Rf=0.39 (9/1 CH2Cl2/methanol). ES MS (m/z): 423 (M+).

Workup

  1. additionTreat a 0° C.
  2. additionTreat
  3. filtrationfilter through hyflo
  4. customRemove the solvent from the filtrate in vacuo
  5. additiondilute the residue with minimal water and brine
  6. extractionextract three times with 3:1 chloroform
  7. dry with materialDry the organic layer (Na2SO4)
  8. customremove the solvent in vacuo
  9. customto afford crude product
  10. custompurify with a 0 to 10% methanol in CH2Cl2 gradient

Sources & evidence

ORD record
ord-b746b5c8094a47dab42a8db4b6584bba
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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