Hydrochloric Acid → HCID 68713392, compound

HRID 1911529Notes

Reaction equation

HRID 1911529 reaction equation
C(OC([N:8]1[C@@H:12](/[CH:13]=[C:14](/[C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)\[CH2:15][CH3:16])[CH2:11][O:10]C1(C)C)=O)(C)(C)C.Cl.[OH-].[Na+]>O1CCOCC1.C(OCC)(=O)C>[NH2:8][C@@H:12](/[CH:13]=[C:14](/[C:17]1[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=1)\[CH2:15][CH3:16])[CH2:11][OH:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68715190HCID 68715190, compound

Product 1

HCID 68713392HCID 68713392, compoundYield 103.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
35 °C

Procedure

To a stirred solution of (S)-4-[(E)-2-(4-chloro-phenyl)-but-1-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (820 mg) at r.t. in dioxane (8 ml) was added 4 M HCl solution in dioxane (11.2 ml). The mixture was stirred at 35° C. for 3.5 h. The mixture was then diluted with ethyl acetate and made basic by addition of 2 N aq sodium hydroxide solution. The phases were separated and the organic phase was washed with saturated brine, dried over sodium sulphate and concentrated in vacuo to give (E)-(S)-2-amino-4-(4-chloro-phenyl)-hex-3-en-1-ol (524 mg, quant.) as a yellow oil. MS (ISP): 228.2 ([{37Cl}M+H]+), 226.2 ([{35Cl}M+H]30).

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with saturated brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-03cd2ce6e5e5452aa3c21df1ef5f408a
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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