Hydrochloric Acid → HCID 57667120, compound

HRID 600839Notes

Reaction equation

HRID 600839 reaction equation
C(OC([N:8]1[C@@H:12]([CH2:13][N:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:19][CH:18]=2)[CH2:15][CH3:16])[CH2:11][O:10]C1(C)C)=O)(C)(C)C.Cl.O1CCOC[CH2:34]1>>[NH2:8][C@@H:12]([CH2:13][N:14]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:19][CH:18]=1)[CH:15]([CH3:16])[CH3:34])[CH2:11][OH:10]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67272192HCID 67272192, compound

Product 1

HCID 57667120HCID 57667120, compoundYield 71%

Procedure

To a stirred solution of (S)-4-{[(4-benzyl-phenyl)-ethyl-amino]-methyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (405 mg; prepared in analogy to example 1.a and 1.b starting from tert-butyl (R)-(+)-4-formyl-2,2-dimethyl-3-oxazolinecarboxylate and 4-benzylaniline) at r.t. in dioxane (5 ml) under an argon atmosphere was added HCl solution (4M in dioxane; 4.77 ml). The mixture was stirred overnight 16 h, then concentrated. The residue was taken up in CH2Cl2/MeOH 95:5 and 1N NaOH. The aqueous phase was back extracted with CH2Cl2/MeOH 95:5. The combined organics were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by column chromatography (Isolute® SPE flash NH2 column, aminopropyl-functionalized silica; gradient:CH2Cl2->CH2Cl2/MeOH 9:1) to give (S)-2-amino-3-[(4-benzyl-phenyl)-isopropyl-amino]-propan-1-ol (192 mg, 71%) as colorless amorphous solid. MS (ISP): 285.3 ([M+H]+)

Workup

  1. concentrationconcentrated
  2. extractionThe aqueous phase was back extracted with CH2Cl2/MeOH 95:5
  3. washThe combined organics were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (Isolute® SPE flash NH2 column, aminopropyl-functionalized silica; gradient:CH2Cl2->CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-b9ab6a5b0ad640e0adf39e6a2dbb8902
Source dataset
uspto-grants-2011_03
Patent number
US07902238B2

Reaction notes

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