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

HRID 1845949Notes

Reaction equation

HRID 1845949 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3][OH:4].O.C(=O)(O)[O-].[Na+].Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]>ClCCl>[OH:4][CH2:3][C:2]([NH:1][C:14](=[O:15])[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 118072-Amino-2-methyl-1-propanolHCID 516892Sodium Bicarbonate

Product 1

HCID 12325553benzyl N-(1-hydroxy-2-methylpropan-2-yl)carbamateYield 101.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.0 g of 2-amino-2-methylpropan-1-ol was dissolved in 100 mL of dichloromethane, and 100 mL of water and 8.4 g of sodium bicarbonate were then added. To this solution, 5.7 g of benzyl chloroformate was added dropwise, and the mixture was stirred at room temperature for 16 hours. After extraction with dichloromethane (100 mL×3), the extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the obtained crude product was purified by silica gel column chromatography (ethyl acetate:hexane=1:1) to obtain 7.6 g of the compound of interest as a colorless oil (86%).

Workup

  1. extractionAfter extraction with dichloromethane (100 mL×3)
  2. dry with materialthe extract was dried over anhydrous sodium sulfate
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated
  5. customthe obtained crude product
  6. customwas purified by silica gel column chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-ffece167821c4075b604bb0f9bf6e740
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Reaction notes

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