Hydrochloric Acid → HCID 68714455, compound

HRID 1911510Notes

Reaction equation

HRID 1911510 reaction equation
C(OC([N:8]1[C@H:12]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([F:21])=[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][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)[CH2:11][OH:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68715897HCID 68715897, compound

Product 1

HCID 68714455HCID 68714455, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of (R)-4-[2-(4-fluoro-phenyl)-ethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (190 mg) at r.t. in dioxane (3.5 ml) under an argon atmosphere was added 4 M HCl solution in dioxane (1.47 ml). The mixture was stirred for 16 h. The mixture was concentrated. The crude product was purified by column chromatography (SiO2; gradient: CH2Cl2->CH2Cl2/MeOH 9:1) to give (R)-2-amino-4-(4-fluoro-phenyl)-butan-1-ol (78 mg) as off-white solid. MS (ISP): 184.1 ([M+H]+))

Workup

  1. concentrationThe mixture was concentrated
  2. customThe crude product was purified by column chromatography (SiO2; gradient: CH2Cl2->CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-57e4fffe9f014bac9b85a8eb621a5098
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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