Tetrahydrofuran → tert-Butyl 4-(hydroxymethyl)phenethylcarbamate

HRID 1048040Notes

Reaction equation

HRID 1048040 reaction equation
O1CCCC1.[C:6]([O:10][C:11]([NH:13][CH2:14][CH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1)=[O:12])([CH3:9])([CH3:8])[CH3:7]>>[OH:21][CH2:20][C:19]1[CH:23]=[CH:24][C:16]([CH2:15][CH2:14][NH:13][C:11](=[O:12])[O:10][C:6]([CH3:9])([CH3:7])[CH3:8])=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 166409054-(2-{[(Tert-butoxy)carbonyl]amino}ethyl)benzoic acid

Product 1

HCID 22337080tert-Butyl 4-(hydroxymethyl)phenethylcarbamateYield 85.2%

Procedure

A 1M solution of borane-tetrahydrofuran complex in tetrahydrofuran (100 mL, 100 mmol) was added directly to solid (4-(2-(tert-butoxycarbonylamino)ethyl)benzoic acid (12.4 g, 46.7 mmol). The resulting solution was stirred at ambient temperature for 1 hour, carefully quenched with water (250 mL), and extracted with ethyl acetate (500 mL). The organic layer was washed with saturated sodium bicarbonate (200 mL) and brine (100 mL), dried over sodium sulfate and concentrated to afford tert-butyl 4-(hydroxymethyl)phenethylcarbamate as a pale yellow oil (10.0 g, 85% yield).

Workup

  1. customcarefully quenched with water (250 mL)
  2. extractionextracted with ethyl acetate (500 mL)
  3. washThe organic layer was washed with saturated sodium bicarbonate (200 mL) and brine (100 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-41c6f7487c9c41febaae7abcefe6b0f2
Source dataset
uspto-grants-2013_10
Patent number
US08569522B2

Reaction notes

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