Hydrochloric Acid → HCID 57667077, compound

HRID 2276367Notes

Reaction equation

HRID 2276367 reaction equation
C(OC([N:8]1[C@@H:12]([CH2:13][N:14]([CH2:21][CH3:22])[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][N:14]([CH2:21][CH3:22])[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 57667060HCID 57667060, compound

Product 1

HCID 57667077HCID 57667077, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of (S)-4-[(ethyl-phenyl-amino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (462 mg) at r.t. in dioxane (5.85 ml) under an argon atmosphere was added HCl solution (4 M in dioxane; 4.14 ml). The mixture was stirred at r.t. overnight and concentrated. The residue was taken up in EtOAc and washed with 10% aq. potassium bicarbonate solution. The aqueous layer was back extracted with EtOAc. The combined organics were washed with water and then with brine, dried over MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography (Isolute® SPE flash NH2 column, aminopropyl-functionalized silica; CH2Cl2/MeOH 9:1) to give (S)-2-amino-3-(ethyl-phenyl-amino)-propan-1-ol (133 mg, 62%) as a light brown viscous oil. MS (ISP): 195.1 ([M+H]+).

Workup

  1. concentrationconcentrated
  2. washwashed with 10% aq. potassium bicarbonate solution
  3. extractionThe aqueous layer was back extracted with EtOAc
  4. washThe combined organics were washed with water
  5. dry with materialwith brine, dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (Isolute® SPE flash NH2 column, aminopropyl-functionalized silica; CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-ddbe66b352c64b7682eae3e8b8a57f3c
Source dataset
uspto-grants-2015_09
Patent number
US09132136B2

Reaction notes

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