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

HRID 605396Notes

Reaction equation

HRID 605396 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].C(N(CC)CC)C.[CH2:14]([O:21][C:22](ON1C(=O)CCC1=O)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[OH:4][CH2:3][C:2]([NH:1][C:22](=[O:23])[O:21][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 118072-Amino-2-methyl-1-propanolHCID 83172Benzyl succinimido carbonate

Product 1

HCID 12325553benzyl N-(1-hydroxy-2-methylpropan-2-yl)carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-amino-2-methylpropan-1-ol (1.0 g, 11.2 mmol), triethylamine (1.7 mL, 12.2 mmol) and N-(benzyloxycarbonyloxy)-succinimide (3.1 g, 12.4 mmol) in THF (100 mL) at 0° C. were reacted for 0.5 hours then at room temperature for an additional hour. The reaction was concentrated and extracted with ethyl acetate (100 mL). The organic extract was washed sequentially with water, brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with a gradient of ethyl acetate in dichloromethane (0-20%) to give the title compound as a colorless oil (2.5 g, quantitative).

Workup

  1. waitat room temperature for an additional hour
  2. concentrationThe reaction was concentrated
  3. extractionextracted with ethyl acetate (100 mL)
  4. extractionThe organic extract
  5. washwas washed sequentially with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by chromatography on silica gel
  9. washeluting with a gradient of ethyl acetate in dichloromethane (0-20%)

Sources & evidence

ORD record
ord-142e24590ca24defab85e952d975db2d
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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