2-(4-BOC-PIPERAZINYL)-2-PHENYLACETIC ACID → HCID 58786718, compound

HRID 1376030Notes

Reaction equation

HRID 1376030 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:21](O)=[O:22])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:21][OH:22])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 27622172-(4-BOC-PIPERAZINYL)-2-PHENYLACETIC ACID

Product 1

HCID 58786718HCID 58786718, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-(Carboxy-phenyl-methyl)-piperazine-1-carboxylic acid tert-butyl ester (351) (10.7 g, 33.43 mmol) in THF (120 mL) at 0° C. was slowly added BH3—SMe2 (6.69 mL, 66.86 mmol). The reaction mixture was allowed to warm to room temperature and then stirred at room temperature for 96 h. The reaction mixture was then quenched with sat. NaHCO3 (120 mL) at 0° C. and diluted with Et2O. The organic phase was dried with MgSO4 and then concentrated to dryness. The crude material was purified by chromatography (silica gel 60 mesh, eluting with 50% EtOAc/50% hexanes); yielding 3.78 g (86%) pure product.

Workup

  1. customat 0° C.
  2. customThe reaction mixture was then quenched with sat. NaHCO3 (120 mL) at 0° C.
  3. additiondiluted with Et2O
  4. dry with materialThe organic phase was dried with MgSO4
  5. concentrationconcentrated to dryness
  6. customThe crude material was purified by chromatography (silica gel 60 mesh, eluting with 50% EtOAc/50% hexanes)

Sources & evidence

ORD record
ord-bcde33df409840a886a9eeebc09c8636
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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