Hydrochloric Acid → HCID 16106975, compound

HRID 1911513Notes

Reaction equation

HRID 1911513 reaction equation
C(OC([N:8]1[C@H:12]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][O:10]C1(C)C)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][C@H:12]([CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:11][OH:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 16106960HCID 16106960, compound

Product 1

HCID 16106975HCID 16106975, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of (R)-2,2-dimethyl-4-phenoxymethyl-oxazolidine-3-carboxylic acid tert-butyl ester (300 mg) at r.t. in dioxane (5 ml) under an argon atmosphere was added 4 M HCl solution in dioxane (2.44 ml). The mixture was stirred for 16 h. The mixture was concentrated. The residue was resuspended in saturated aq sodium carbonate solution and the mixture was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated in vacuo. The crude product was purified by column chromatography (SiO2; gradient: CH2Cl2->CH2Cl2/MeOH 9:1) to give (S)-2-amino-3-phenoxy-propan-1-ol (108 mg, 66%) as a white solid. MS (ISP): 168.3 ([M+H]+)).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography (SiO2; gradient: CH2Cl2->CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-4087b1c982364bedb9b556f616e4b24e
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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