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

HRID 884013Notes

Reaction equation

HRID 884013 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-b96abf114e104a84aa9cdc24c636c9f8
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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