Water → 6-(Benzyloxy)-7-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 1944215Notes

Reaction equation

HRID 1944215 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[C:15]([CH3:21])=[N:14][CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O.[Cl-].[Na+]>CCO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[CH:15]([CH3:21])[NH:14][CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 409929HCID 409929, compoundHCID 4311764Sodium borohydride

Product 1

HCID 6226266-(Benzyloxy)-7-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinolineYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 249 (949 mg, 3.4 mmol) in EtOH (15 ml) at 0° C. was added sodium borohydride (256 mg, 6.8 mmol) portionwise. The reaction mixture was stirred at rt for 1.5 h. Water (100 ml) was added and the aqueous layer was neutralised. The aqueous layer was saturated with sodium chloride and extracted with EtOAc (3×100 ml). The combined organic layers were washed with sat. aq. sodium hydrogen C(Ar)bonate (100 ml), dried (MgSO4) and concentrated in vacuo to afford the title compound (600 mg, 63%) a yellow oil. 1H NMR (400 MHz; DMSO-d6) 1.58 (3H, d, J=6.4 Hz, CH3CH), 2.50 (2H, s, CH2), 2.82-2.95 (2H, m, CH2), 3.76 (3H, s, OCH3), 4.42 (1H, q, J=6.4 Hz, CH3CH), 5.06 (2H, s, CH2Ph), 6.86 (1H, s, CH), 6.88 (1H, s, CH), 7.31-7.44 (5H, m, 5×CH, phenyl), 9.40 (1H, brs, NH). LC/MS (ES+) tr=0.73 min, m/z 284.13 (M++H).

Workup

  1. extractionextracted with EtOAc (3×100 ml)
  2. washThe combined organic layers were washed with sat. aq. sodium hydrogen C(Ar)bonate (100 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a32f2bf8127d471b893166a94eecfbe7
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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