Diisopropylethylamine → Carbamic acid, N-((1R)-2-hydroxy-1-phenylethyl)-, 1,1-dimethylethyl ester

HRID 1028507Notes

Reaction equation

HRID 1028507 reaction equation
[NH2:1][C@H:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH2:3][OH:4].[O:11](C(OC(C)(C)C)=O)[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=O.CCN(C(C)C)C(C)C>C(Cl)Cl.CCOC(C)=O>[OH:4][CH2:3][C@H:2]([NH:1][C:12](=[O:11])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 2724025(R)-beta-aminophenethyl alcohol

Product 1

HCID 7016461Carbamic acid, N-((1R)-2-hydroxy-1-phenylethyl)-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R)-2-amino-2-phenylethanol (400 mg, 2.91 mmol) in CH2Cl2 (15 mL) was added BOC2O (636 mg, 2.91 mmol) and DIPEA (507 μL, 2.91 mmol). The reaction was stirred at room temperature for 18 hours, diluted with EtOAc (75 mL) and washed with H2O, brine, 1N HCl, brine, saturated NaHCO3, and brine (25 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography with 50% EtOAc/hexanes afforded tert-butyl [(1R)-2-hydroxy-1-phenylethyl]carbamate. Rf=0.23 (40% EtOAc/hexane). 1H NMR (CDCl3, 600 MHz) δ 7.27-7.37 (m, 5H), 5.27 (bs, 1H), 4.78 (bs, 1H), 3.83 (bs, 2H), 2.46 (bs, 1H), 1.44 (bs, 9H).

Workup

  1. washwashed with H2O, brine, 1N HCl, brine, saturated NaHCO3, and brine (25 mL each)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue by flash chromatography with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-dc406e70fd4546f3b2a43a9f6565b068
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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