Hydrochloric Acid → rac-3-Amino-7,7,7-trifluoro-2-methylheptan-2-ol hydrochloride

HRID 1844172Notes

Reaction equation

HRID 1844172 reaction equation
C1CCCCC=1.[F:7][C:8]([F:29])([F:28])[CH2:9][CH2:10][CH2:11][CH:12]([NH:17]C(=O)OCC1C=CC=CC=1)[C:13]([OH:16])([CH3:15])[CH3:14].[ClH:30]>[Pd].C(O)C.C(OCC)C>[ClH:30].[NH2:17][CH:12]([CH2:11][CH2:10][CH2:9][C:8]([F:7])([F:28])[F:29])[C:13]([CH3:14])([OH:16])[CH3:15]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 8079CyclohexeneHCID 86718190Rac-benzyl (7,7,7-trifluoro-2-hydroxy-2-methylheptan-3-yl)carbamate

Product 1

HCID 86718188rac-3-Amino-7,7,7-trifluoro-2-methylheptan-2-ol hydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Under argon, 319 mg (0.30 mmol, 10% pure) of palladium on activated carbon and 9.1 ml (90.0 mmol) of cyclohexene were added to 1.0 g (3.0 mmol) of rac-benzyl (7,7,7-trifluoro-2-hydroxy-2-methylheptan-3-yl)carbamate Example 101A in ethanol (21 ml), and the reaction mixture was stirred at reflux overnight. The mixture was filtered through a Millipore® filter and the filter cake was washed with ethanol. 3 ml (6.0 mmol) of 2 N hydrochloric acid in diethyl ether were added to the filtrate and the mixture was concentrated and dried under high vacuum. This gave 785 mg (111% of theory) of the target compound. The product was used without further purification for the next reaction.

Workup

  1. temperatureat reflux overnight
  2. filtrationThe mixture was filtered through a Millipore®
  3. filtrationfilter
  4. washthe filter cake was washed with ethanol
  5. concentrationthe mixture was concentrated
  6. customdried under high vacuum
  7. customThe product was used without further purification for the next reaction

Sources & evidence

ORD record
ord-2580e189d25b40c188c7e66cfd078609
Source dataset
uspto-grants-2015_02
Patent number
US08946215B2

Reaction notes

Loading…