Triethylamine → benzyl N-(1-hydroxy-2-phenylpropan-2-yl)carbamate

HRID 605405Notes

Reaction equation

HRID 605405 reaction equation
Cl.[NH2:2][C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[CH2:4][OH:5].[CH2:13]([O:20][C:21](ON1C(=O)CCC1=O)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C1COCC1>[OH:5][CH2:4][C:3]([NH:2][C:21](=[O:22])[O:20][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 83172Benzyl succinimido carbonateHCID 670404922-Amino-2-phenylpropan-1-ol hydrochloride

Product 1

HCID 24787383benzyl N-(1-hydroxy-2-phenylpropan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-2-phenylpropan-1-ol hydrochloride (0.5 g, 2.7 mmol) was reacted with N-(benzyloxycarbonyloxy)-succinimide (0.73 g, 2.9 mmol) and triethylamine (0.82 mL, 5.9 mmol) in THF (25 mL) at 0° C. for 1.0 hours and then at room temperature for 1 hour. The reaction was concentrated and extracted with ethyl acetate (25 mL). The extract was washed with water (2×) and brine, dried over MgSO4, and concentrated to give the crude title compound and used without further purification.

Workup

  1. concentrationThe reaction was concentrated
  2. extractionextracted with ethyl acetate (25 mL)
  3. washThe extract was washed with water (2×) and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8d47778fb4d3415d9f9c3f80fbbdf66f
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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