Hydrochloric Acid → HCID 66514643, compound

HRID 1850103Notes

Reaction equation

HRID 1850103 reaction equation
[C:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[CH:5][C:4]([C@H:7]([NH:10]C(=O)OC(C)(C)C)[CH2:8][OH:9])=[CH:3][CH:2]=1.Cl>CO>[NH2:10][C@@H:7]([C:4]1[CH:5]=[CH:6][C:1]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:2][CH:3]=1)[CH2:8][OH:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86730134HCID 86730134, compound

Product 1

HCID 66514643HCID 66514643, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-tert-butyl 1-(biphenyl-4-yl)-2-hydroxyethylcarbamate (608 mg, 1.940 mmol) in MeOH (3 mL) was added HCl (4M in dioxane, 8 mL) at room temperature. The mixture was stirred for 1 hour and concentrated under reduced pressure. The residue was dissolved in DCM (10 mL)/water (1.0 mL) and stirred with NaHCO3 for 1 hour. The mixture was filtered off and rinsed with DCM. The filtrate was dried over sodium sulfate, filtered off and concentrated under reduced pressure providing (S)-2-amino-2-(biphenyl-4-yl)ethanol (171 mg) as a white solid. LCMS m/z 214.2 (M+H)+, Rt 0.58 min.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in DCM (10 mL)/water (1.0 mL)
  3. stirringstirred with NaHCO3 for 1 hour
  4. filtrationThe mixture was filtered off
  5. washrinsed with DCM
  6. dry with materialThe filtrate was dried over sodium sulfate
  7. filtrationfiltered off
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9328d655a5f34808b2b90b37f276e88a
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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