Sodium Hydroxide → HCID 86732206, compound

HRID 930378Notes

Reaction equation

HRID 930378 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@:8]([NH:18][S@@](C(C)(C)C)=O)([CH2:11][C@H:12]([OH:17])[C:13]([F:16])([F:15])[F:14])[CH2:9][F:10])[CH:5]=[CH:6][CH:7]=1.O1CCOCC1.[OH-].[Na+]>ClCCl.Cl>[NH2:18][C@@:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=1)([CH2:9][F:10])[CH2:11][C@H:12]([OH:17])[C:13]([F:15])([F:16])[F:14]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 86732204HCID 86732204, compound

Product 1

HCID 86732206HCID 86732206, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

(R)-N-((2S,4S)-2-(3-bromophenyl)-1,5,5,5-tetrafluoro-4-hydroxypentan-2-yl)-2-methylpropane-2-sulfinamide (1.83 g, 4.21 mmol) was dissolved in dichloromethane 37 mL and hydrogen chloride, 4.0M solution in 1,4-dioxane (5.27 ml, 21.07 mmol) was added dropwise. The reaction was stirred at room temperature for 10 min. The reaction was worked up by addition of 1N NaOH and extraction with dichloromethane three times. The combined organic layers were dried over sodium sulfate, filtered and concentrated to afford (2S,4S)-4-amino-4-(3-bromophenyl)-1,1,1,5-tetrafluoropentan-2-ol that was used without further purification.

Workup

  1. dry with materialThe combined organic layers were dried over sodium sulfate
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-03d1b714687f45bbba73d9f515ff6b29
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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