Di-tert-butyl dicarbonate → (4-Hydroxybenzyl)phenethylcarbamic acid tert-butyl ester

HRID 492418Notes

Reaction equation

HRID 492418 reaction equation
[CH2:1]([NH:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:18](C(OC(C)(C)C)=O)[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=O>ClCCl>[C:22]([O:21][C:19](=[O:18])[N:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)[CH2:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 30425764-(Phenethylaminomethyl)phenol

Product 1

HCID 59729945(4-Hydroxybenzyl)phenethylcarbamic acid tert-butyl esterYield 52.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Suspend 4-(phenethylaminomethyl)phenol (0.750 g, 3.30 mmol) in dichloromethane (10 mL). Add a solution of (BOC)2O (1.08 g, 4.95 mmol) in dichloromethane (6.5 mL). Quench with 1.0 N NaOH (75 mL) after 19 hours. Extract with dichloromethane (2× 200 mL). Wash the organic layer with brine (1× 75 mL), dry over Na2SO4, filter and concentrate. Purify by flash chromatography, eluting with 20-30% ethyl acetate in hexanes to give the title compound (0.570 g, 52.8%): MS ES+ 328.3 (M+H)+, base peak ES+ 272.1 (M+2H—C(CH3)3)+, ES− 326.3 (M−H)−; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 30-99% over 19 min], tR=14.7 min, 100% purity.

Workup

  1. customQuench with 1.0 N NaOH (75 mL) after 19 hours
  2. extractionExtract with dichloromethane (2× 200 mL)
  3. washWash the organic layer with brine (1× 75 mL)
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify by flash chromatography
  8. washeluting with 20-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f661937f1b3a4707ac51388fe23ef64c
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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