Ammonium formate → Tert-butyl 4-[(1-hydroxycyclohexyl)[4-hydroxy-3-(trifluoromethoxy)phenyl]acetyl}piperazine-1-carboxylate

HRID 28844Notes

Reaction equation

HRID 28844 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([C:31]2([OH:37])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)[C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)=[O:17])=[CH:11][C:10]=1[O:38][C:39]([F:42])([F:41])[F:40])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[OH:37][C:31]1([CH:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([O:38][C:39]([F:41])([F:42])[F:40])[CH:11]=2)[C:16]([N:18]2[CH2:19][CH2:20][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:22][CH2:23]2)=[O:17])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68852993tert-Butyl 4-[[4-(benzyloxy)-3-(trifluoromethoxy)phenyl](1-hydroxycyclohexyl)acetyl]piperazine-1-carboxylate

Product 1

HCID 68855865Tert-butyl 4-[(1-hydroxycyclohexyl)[4-hydroxy-3-(trifluoromethoxy)phenyl]acetyl}piperazine-1-carboxylateYield 70.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-Butyl 4-[[4-(benzyloxy)-3-(trifluoromethoxy)phenyl](1-hydroxycyclohexyl)acetyl]piperazine-1-carboxylate (1.7 g, 2.87 mmol) (See Example 268, Step 5), ammonium formate (0.95 g, 15.0 mmol), and a catalytic amount of palladium on carbon was heated at 50° C. for 1 hr in methanol (25 mL). At the end of this time the solution was concentrated and the residue taken up in ethyl acetate and filtered through a plug of silica gel eluting with 30% ethyl acetate:hexane. The filtrate was concentrated to afford 1.02 g of tert-butyl 4-[(1-hydroxycyclohexyl)[4-hydroxy-3-(trifluoromethoxy)phenyl]acetyl}piperazine-1-carboxylate. MS (ESI) m/z 503; HRMS: calcd for C24H33F3N2O6+H+, 503.23635; found (ESI, [M+H]+), 503.2343.

Workup

  1. concentrationAt the end of this time the solution was concentrated
  2. filtrationfiltered through a plug of silica gel eluting with 30% ethyl acetate
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-edccbbdc45354ba6b77bf3132693b323
Source dataset
uspto-grants-2008_09
Patent number
US07419980B2

Reaction notes

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