HCID 70982841, compound → HCID 86731996, compound

HRID 2283491Notes

Reaction equation

HRID 2283491 reaction equation
C([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH3:18])=[O:16])[CH:11]([O:19][CH3:20])[CH2:10]1)C1C=CC=CC=1.[H][H]>CO.[OH-].[OH-].[Pd+2]>[NH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH3:18])=[O:16])[CH:11]([O:19][CH3:20])[CH2:10]1

Participants

5

Reactant 2

HCID 70982841HCID 70982841, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 86731996HCID 86731996, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 887MethanolSolvent

Procedure

Methyl 4-(benzylamino)-2-methoxycyclohexanecarboxylate (1.84 g, 6.63 mmol, racemic mixture of diastereomers) and palladium hydroxide on carbon (20 weight %, 0.233 g, 0.332 mmol) in methanol (35 mL) were combined, and the atmosphere was exchanged for hydrogen (balloon) via four vacuum hydrogen flush cycles. After 24 hours, additional palladium hydroxide on carbon (20 weight %, 0.233 g, 0.332 mmol) was added, and the reaction mixture was again placed under a hydrogen atmosphere. Following another 24 hours, the reaction mixture was filtered through diatomaceous earth and concentrated under reduced pressure to give methyl 4-amino-2-methoxycyclohexanecarboxylate as a racemic mixture of three diastereomers, which was carried forward without further purification. MS ESI calcd. for C9H18NO3 [M+H]+ 188. found 188.

Workup

  1. customflush cycles
  2. waitFollowing another 24 hours
  3. filtrationthe reaction mixture was filtered through diatomaceous earth
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fc2d3f699dac4e95b4dfb69ba06b623b
Source dataset
uspto-grants-2015_09
Patent number
US09145391B2

Reaction notes

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