Iodine → 2-Amino-2-(4-chlorophenyl)ethan-1-ol

HRID 423043Notes

Reaction equation

HRID 423043 reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH:7]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)(=[O:4])=[O:3].[NH2:23][CH:24]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[C:25](O)=[O:26].[BH4-].[Na+].II>C1COCC1>[CH3:1][S:2]([O:5][CH2:6][CH:7]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)(=[O:3])=[O:4].[NH2:23][CH:24]([C:28]1[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=1)[CH2:25][OH:26]

Participants

7

Reactant 4

HCID 807IodineHCID 587821Benzeneacetic acid, alpha-amino-4-chloro-HCID 4311764Sodium borohydrideHCID 577502782-(Tert-butoxycarbonylamino)-2-(4-chlorophenyl)ethyl methanesulfonate

Product 2

HCID 148531952-Amino-2-(4-chlorophenyl)ethan-1-olYield 11.88%HCID 577502782-(Tert-butoxycarbonylamino)-2-(4-chlorophenyl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The tert-butyl 1-(4-chlorophenyl)-2-hydroxyethylcarbamate used in the above reaction was prepared as follows. 2-Amino-2-(4-chlorophenyl)acetic acid (12 g, 64.65 mmol) was stirred in THF (200 mL) and sodium borohydride (5.82 g, 153.87 mmol) was added in portions to the stirred mixture under nitrogen. A solution of iodine (16.41 g, 64.65 mmol) in THF (20 mL) was added dropwise maintaining the temperature below 15° C. using an ice bath. The resulting mixture was warmed to room temperature and stirred at reflux overnight. The reaction was quenched by the addition of methanol (40 mL). A portion of this solution was removed (50 mL) and partitioned between ethyl acetate and water. The organic layer was concentrated under reduced pressure. The residue was purified by MPLC on silica using gradient elution (0 to 10% methanol/DCM). The desired product, 2-amino-2-(4-chlorophenyl)ethanol (1.318 g, 11.88%), was thus isolated as a colourless solid.

Workup

  1. customwas prepared
  2. temperaturemaintaining the temperature below 15° C.
  3. temperatureat reflux overnight
  4. customThe reaction was quenched by the addition of methanol (40 mL)
  5. customA portion of this solution was removed (50 mL)
  6. custompartitioned between ethyl acetate and water
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. customThe residue was purified by MPLC on silica using gradient elution (0 to 10% methanol/DCM)

Sources & evidence

ORD record
ord-5a5d84c282d3452bb8ddb737e69c9c3e
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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