HCID 18700106, compound → HCID 54030415, compound

HRID 2289308Notes

Reaction equation

HRID 2289308 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[C:17]([C:24]([F:27])([F:26])[F:25])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.C([O-])(O)=O.[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:23]=[CH:22][C:18]([CH2:19][OH:20])=[C:17]([C:24]([F:27])([F:25])[F:26])[CH:16]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 18700106HCID 18700106, compound

Product 1

HCID 54030415HCID 54030415, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-(N-tert-butyloxy-carbonyl-4-piperidinyloxy)-2-trifluoromethylbenzoic acid (0.66 g, 2.3 mmol) from Step 2 above in THF (10 mL) at 0° C. was added BH3.THF complex (3.5 mL of a 1.0 M solution in THF, 3.5 mmol). The solution was stirred at 0° C. for 1 h and then at ambient temperature for 14 h. The solution was diluted with saturated aqueous NaHCO3 (25 mL) and the solvents were removed under reduced pressure. The residue was partitioned between EtOAc (50 mL) and water (2×25 mL). The organic phase was dried (MgSO4), filtered, and the solvent was removed under reduced pressure to give 4-(N-tert-butyloxycarbonyl-4-piperidinyloxy)-2-trifluoromethylbenzyl alcohol as a colorless gum (HPLC retention time=10.2 min (method A)).

Workup

  1. waitat ambient temperature for 14 h
  2. customthe solvents were removed under reduced pressure
  3. customThe residue was partitioned between EtOAc (50 mL) and water (2×25 mL)
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-e64a2709888949d5b877540db0d2d368
Source dataset
uspto-grants-2000_07
Patent number
US06090805

Reaction notes

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