Ammonium formate → Compound 18

HRID 722402Notes

Reaction equation

HRID 722402 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][C@@H:16]([C:18]3[CH:32]=[CH:31][C:21]([O:22][CH2:23][C@@H:24]([N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[CH3:25])=[CH:20][CH:19]=3)[C@@H:15]([C:33]3[CH:38]=[CH:37][C:36]([O:39][Si](C(C)C)(C(C)C)C(C)C)=[CH:35][CH:34]=3)[S:14][C:13]=2[CH:50]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.CCOC(C)=O.O.[Pd]>[OH:39][C:36]1[CH:37]=[CH:38][C:33]([C@H:15]2[S:14][C:13]3[CH:50]=[C:9]([OH:8])[CH:10]=[CH:11][C:12]=3[O:17][C@H:16]2[C:18]2[CH:32]=[CH:31][C:21]([O:22][CH2:23][C@@H:24]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[CH3:25])=[CH:20][CH:19]=2)=[CH:34][CH:35]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 587430611-{(1S)-2-[4-((2S,3R)-6-(benzyloxy)-3-{4-[(triisopropylsilyl)oxy]phenyl}-2,3-dihydro-1,4-benzoxathiin-2-yl)phenoxy]-1-methylethyl}pyrolidine

Product 1

HCID 449208Compound 18

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 86601158Ethanol ethyl acetate waterSolvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of 102 mg (0.14 mmol) of compound 10a, generated in Example 10, Step A, 30.6 mg (0.29 mmol) of palladium black and 181.2 mg (0.29 mmol) ammonium formate in 3 mL of EtOH/EtOAc/H2O (7:2:1) was heated at 80° C. for 2 h. The reaction mixture was filtered through a pad of Celite® to remove the catalyst, washed thoroughly with EtOH/EtOAc/H2O (7:2:1), and the filtrate was partitioned between water and EtOAc. The organic phase was separated, dried over Na2SO4, filtered, evaporated, and dried in vacuo to give the crude product which was used without purification.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. customto remove the catalyst
  3. washwashed thoroughly with EtOH/EtOAc/H2O (7:2:1)
  4. customthe filtrate was partitioned between water and EtOAc
  5. customThe organic phase was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customdried in vacuo

Sources & evidence

ORD record
ord-1ce3b14e8f5048ebb4648f2a35f88b26
Source dataset
uspto-grants-2006_11
Patent number
US07138426B2

Reaction notes

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