Boron tribromide → 6-Hydroxy-4,4-dimethyl-1,2,3,4-tetrahydro-isoquinoline-2-carbaldehyde

HRID 2185216Notes

Reaction equation

HRID 2185216 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([CH:13]=[O:14])[CH2:7][C:6]2([CH3:16])[CH3:15].COC1C2C(=CC=CC=2)C(C)(C)CN1C=O.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([CH:13]=[O:14])[CH2:7][C:6]2([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 22459799HCID 22459799, compoundHCID 225688096-Methoxy-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde

Product 1

HCID 225688696-Hydroxy-4,4-dimethyl-1,2,3,4-tetrahydro-isoquinoline-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred, cooled (−78° C.) solution of 6-methoxy-4,4-dimethyl-1,2,3,4-tetrahydro-isoquinoline-2-carbaldehyde (Intermediate 19, 3.26 g, 15 mmol) in anhydrous dichloromethane (15 mL) was treated with 1M solution of boron tribromide in dichloromethane (50 mL) stirred at ambient temperature for 3 h. It was then cooled again to 78° C. and quenched carefully with saturated aqueous sodium carbonate solution, diluted with water and the aqueous phase was extracted with ethyl acetate (×2). The combined organic extract was dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to afford the title compound as a solid foam (3 g, 99%).

Workup

  1. temperatureIt was then cooled again to 78° C.
  2. customquenched carefully with saturated aqueous sodium carbonate solution
  3. additiondiluted with water
  4. extractionthe aqueous phase was extracted with ethyl acetate (×2)
  5. extractionThe combined organic extract
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-aaf2f2d5592f40beb20e08e32df8ccd9
Source dataset
uspto-grants-2002_06
Patent number
US06399774B1

Reaction notes

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