HCID 58841363, compound → Tert-butyl 6-(1-hydroxyethyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate

HRID 32114Notes

Reaction equation

HRID 32114 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]=[O:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:21][Mg+].[Br-]>C1COCC1>[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[C:17]2[C:12](=[CH:13][C:14]([CH:18]([OH:19])[CH3:21])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 58841363HCID 58841363, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 68681678Tert-butyl 6-(1-hydroxyethyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of (6-formyl-1,2,3,4-tetrahydro-naphthalen-1-yl)-carbamic acid tert-butyl ester (Step c, 2.80 g, 10.2 mmol, 1.0 eq) in THF (100 mL) at −78° C. was added a solution of MeMgBr (Aldrich, 1.4 M in toluene/THF (3:1), 29 mL, 40.7 mmol, 4.0 eq) slowly. The reaction was stirred at −78° C. for 20 min, warmed to RT and stirred at RT for 2 h. The reaction was quenched with saturated NaHCO3 (120 mL), and the crude was extracted with EtOAc (100 mL×3). The extract phase was washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. The title compound was obtained as a white solid. MS (ESI, pos. ion) m/z: 292 (M+1).

Workup

  1. temperaturewarmed to RT
  2. stirringstirred at RT for 2 h
  3. customThe reaction was quenched with saturated NaHCO3 (120 mL)
  4. extractionthe crude was extracted with EtOAc (100 mL×3)
  5. washThe extract phase was washed with saturated NaCl
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-662ccd5a5fa843af9d54d6491a773466
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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