Hydrochloric Acid → HCID 67228627, compound

HRID 1026150Notes

Reaction equation

HRID 1026150 reaction equation
C(OC([N:8]1[C@@H:12]([CH2:13][CH2:14][CH:15]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=2)[CH2:16][CH3:17])[CH2:11][O:10]C1(C)C)=O)(C)(C)C.Cl>C(O)C>[NH2:8][C@@H:12]([CH2:13][CH2:14][CH:15]([C:18]1[CH:19]=[C:20]([F:25])[CH:21]=[C:22]([F:24])[CH:23]=1)[CH2:16][CH3:17])[CH2:11][OH:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67176876HCID 67176876, compound

Product 1

HCID 67228627HCID 67228627, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To (S)-4-[3-(3,5-difluoro-phenyl)-pentyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (0.5 g) was added under an argon atmosphere 5.5 M HCl solution in ethanol (2 ml). The mixture was stirred for 16 h. The mixture was concentrated. The residue was dissolved in dichloromethane and an excess of ammonia in methanol and some silica gel was added. The solvents were evaporated and the crude product was purified by column chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: dichloromethane/methanol=90:10) to give (S)-2-amino-5-(3,5-difluoro-phenyl)-heptan-1-ol (0.27 g) as a colourless liquid. MS (ISP): 244.3 ([M+H]+).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was dissolved in dichloromethane
  3. additionan excess of ammonia in methanol and some silica gel was added
  4. customThe solvents were evaporated
  5. customthe crude product was purified by column chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: dichloromethane/methanol=90:10)

Sources & evidence

ORD record
ord-fc9d353a73034b0492131080804883c2
Source dataset
uspto-grants-2014_05
Patent number
US08729113B2

Reaction notes

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