Triethylamine → 1,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

HRID 2204990Notes

Reaction equation

HRID 2204990 reaction equation
[NH2:1][C@@H:2]([CH3:5])[CH2:3][OH:4].[C:6](=O)([O:12]C(C)(C)C)[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].C(N(CC)CC)C>C1COCC1>[OH:4][CH2:3][C@@H:2]([NH:1][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 80307L-AlaninolHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 70231031,1-Dimethylethyl N-((1S)-2-hydroxy-1-methylethyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-aminopropan-1-ol (1 eq) in THF (0.3 M) at room temperature was added di-tert-butyl carbonate (1 eq) and triethylamine (1 eq). The reaction was stirred at room temperature for 3 hours. The reaction mixture was concentrated en vaccuo; and the residue was diluted in ethyl acetate. The organic solution was washed with water (2×), 1:1 saturated aqueous NH4Cl, water and brine, dried over anhydrous MgSO4, and concentrated en vaccuo. The material was carried onto the next step without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated en vaccuo
  2. additionand the residue was diluted in ethyl acetate
  3. washThe organic solution was washed with water (2×), 1:1 saturated aqueous NH4Cl, water and brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated en vaccuo
  6. customThe material was carried onto the next step without further purification

Sources & evidence

ORD record
ord-58cf9bfd4d9c402a919bbe5b001e8900
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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