Borane → HCID 58786487, compound

HRID 1376046Notes

Reaction equation

HRID 1376046 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH2:15][NH2:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B.[OH-].[Na+].[CH2:27]1COCC1>CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[F:23])[CH2:15][NH:16][CH3:27])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 6331BoraneHCID 8028Tetrahydrofuran2×HCID 14798Sodium HydroxideHCID 587864641,1-Dimethylethyl 4-[2-amino-1-(2-fluorophenyl)ethyl]-1-piperazinecarboxylate

Product 1

HCID 58786487HCID 58786487, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

To Ethoxycarbonylamino-1-(2-fluoro-phenyl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester (207) (1.05 g, 3 mmol) in THF (10 mL) at −78° C. was added 1M borane in THF (4.5 mL). The reaction is stirred at −78° C. for 1 h and then was allowed to warm to room temperature (2 h). 5N aqueous sodium hydroxide was then added and the reaction was allowed to stir for 2 h. The reaction mixture was then diluted with EtOAc and the layers are separated. The organic phase was dried with sodium sulfate and concentrated to dryness yielding 0.95 g (94%) product.

Workup

  1. temperatureto warm to room temperature (2 h)
  2. stirringto stir for 2 h
  3. customthe layers are separated
  4. dry with materialThe organic phase was dried with sodium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9aad269ba2724491a32c614cb4b19d8f
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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