tert-Butyl 1-[3-(benzylamino)-4-fluorobenzyl]cyclopropanecarboxylate → tert-Butyl 1-(3-amino-4-fluorobenzyl)cyclopropanecarboxylate

HRID 626410Notes

Reaction equation

HRID 626410 reaction equation
C([NH:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:12][C:13]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]1)C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[NH2:8][C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:12][C:13]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]1

Participants

4

Reactant 1

HCID 58136659tert-Butyl 1-[3-(benzylamino)-4-fluorobenzyl]cyclopropanecarboxylate

Product 1

HCID 58136688tert-Butyl 1-(3-amino-4-fluorobenzyl)cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

145.0 g (407.9 mmol) of tert-butyl 1-[3-(benzylamino)-4-fluorobenzyl]cyclopropanecarboxylate were dissolved in 1450 ml of ethanol, and 9.67 g of palladium hydroxide (20% on carbon) were added. The suspension was stirred at RT under a hydrogen atmosphere at standard pressure for 18 h. The reaction mixture was then filtered off with suction through kieselguhr, and the filtrate was concentrated. After drying under high vacuum, 500 ml of pentane were added to the residue, resulting in the precipitation of the product. The suspension was stirred in an ice bath for 1 h. The solid was then filtered off with suction, washed twice with pentane and dried under high vacuum. 88.5 g (73.6% of theory) of the title compound were thus obtained.

Workup

  1. filtrationThe reaction mixture was then filtered off with suction through kieselguhr
  2. concentrationthe filtrate was concentrated
  3. dry with materialAfter drying under high vacuum, 500 ml of pentane
  4. additionwere added to the residue
  5. customresulting in the precipitation of the product
  6. stirringThe suspension was stirred in an ice bath for 1 h
  7. filtrationThe solid was then filtered off with suction
  8. washwashed twice with pentane
  9. customdried under high vacuum

Sources & evidence

ORD record
ord-e9932671c9f54a9aa732e04f2d3b85a2
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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