Hydrochloric Acid → (S)-2-amino-4-(4-chloro-phenoxy)-butan-1-ol

HRID 1026103Notes

Reaction equation

HRID 1026103 reaction equation
C(OC([N:8]1[C@@H:12]([CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C.Cl>C(O)C>[NH2:8][C@@H:12]([CH2:13][CH2:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=1)[CH2:11][OH:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67177859(S)-4-[2-(4-chloro-phenoxy)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 57191497(S)-2-amino-4-(4-chloro-phenoxy)-butan-1-olYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To (S)-4-[2-(4-chloro-phenoxy)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (530 mg) 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-4-(4-chloro-phenoxy)-butan-1-ol (185 mg, 58%) as a white solid. MS (ISP): 216.3 ([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-9e9cc3593ffa483fb8f290b5aa390e70
Source dataset
uspto-grants-2014_05
Patent number
US08729113B2

Reaction notes

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