Hydrochloric Acid → Methyl 4-amino-3-methyloxane-3-carboxylate hydrochloride

HRID 736782Notes

Reaction equation

HRID 736782 reaction equation
[CH3:1][C:2]1([C:17]([O:19][CH3:20])=[O:18])[C@H:7]([NH:8][C@@H](C2C=CC=CC=2)C)[CH2:6][CH2:5][O:4][CH2:3]1.[ClH:21]>CO.[OH-].[OH-].[Pd+2]>[ClH:21].[NH2:8][CH:7]1[CH2:6][CH2:5][O:4][CH2:3][C:2]1([CH3:1])[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68821088(4R)-methyl 3-methyl-4-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-3-carboxylate

Product 1

HCID 68817485Methyl 4-amino-3-methyloxane-3-carboxylate hydrochloride

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

(4R)-Methyl 3-methyl-4-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-3-carboxylate (1.37 g, 4.94 mmol) in methanol (70 mL) was treated with 10% palladium hydroxide on carbon (0.42 g, 3.5% mol) and aqueous 1N HCl (7 mL, 1.4 eq) and stirred under a hydrogen balloon for 72 h. The catalyst was removed by filtration. Removal of solvent provided crude methyl 4-amino-3-methyl-tetrahydro-2H-pyran-3-carboxylate hydrochloride that was used in the next step without further purification. MS: (M+H)+=174.1.

Workup

  1. customThe catalyst was removed by filtration
  2. customRemoval of solvent

Sources & evidence

ORD record
ord-d96b93a08f6a46a9b5a98ca2628c6b7c
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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