Ammonia → (βR)-β-Amino-α,α-dimethylbenzeneethanol

HRID 2392831Notes

Reaction equation

HRID 2392831 reaction equation
COC([C@@H:5]([NH2:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.Cl.[CH3:14][Mg]I.[Cl-].[NH4+].N.C([O:22][CH2:23][CH3:24])C>>[NH2:12][C@H:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:23]([CH3:24])([OH:22])[CH3:14]

Participants

6

Reactant 5

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 11217910(S)-(+)-2-Phenylglycine methyl ester hydrochlorideHCID 178418373HCID 178418373, compound

Product 1

HCID 11240681(βR)-β-Amino-α,α-dimethylbenzeneethanolYield 41%

Procedure

D-Phenylglycine methyl ester hydrochloride (12) (5 g, 24.83 mmol) was added in portions, during 15 minutes, to a solution of methylmagnesium iodide [prepared from methyl iodide (9.28 ml, 148.97 mmol)] in diethyl ether (190 ml) and stirred for 3 hours. To promote hydrolysis, a saturated solution of ammonium chloride was added dropwise with vigorous stirring. The insoluble product was filtered off through celite, and the organic layer was separated and dried with sodium sulphate. Concentration in vacuo gave a colourless oil. The aqueous layer was made alkaline by addition of aqueous ammonia. The product was extracted with diethyl ether, dried with sodium sulphate and concentrated in vacuo. The oily residues were then combined and distilled to give the title compound (13) (1.66 g, 41%) as a solid which was recrystallised from 40-60 petroleum-ether; mp 49° C.; [α]D25 (c 1 in CHCl3) -23.2; (Found: C, 72.83; H, 9.05; N, 8.30. C10H15NO requires C, 72.69; H, 9.15; N, 8.48%); δH (200 MHz; CDCl3) 1.04 (3H, s, C(CH3)3), 1.21 (3H, s, C(CH3)3), 2.16 (3H, s, NH2 and OH), 3.39 (1H, s, CHPh), 7.27-7.34 (5H, m, ArCH); δC (125 MHz; CDCl3) 24.69 (CH3), 27.55 (CH3), 64.54 (CH), 72.26 (C), 127.48 (ArCH), 128.05 (ArCH), 128.23 (ArCH), 142.82 (C) ; m/z (CI+, NH3) 166 (M+ +1).

Workup

  1. customhydrolysis
  2. filtrationThe insoluble product was filtered off through celite
  3. customthe organic layer was separated
  4. dry with materialdried with sodium sulphate
  5. concentrationConcentration in vacuo
  6. customgave a colourless oil
  7. extractionThe product was extracted with diethyl ether
  8. dry with materialdried with sodium sulphate
  9. concentrationconcentrated in vacuo
  10. distillationdistilled

Sources & evidence

ORD record
ord-2bf14663040e421c99500e3c103a6573
Source dataset
uspto-grants-1998_09
Patent number
US05801249

Reaction notes

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