Acetic Acid → HCID 58958113, compound

HRID 914983Notes

Reaction equation

HRID 914983 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([NH:12][C:13]2[CH:14]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]=O)[CH:20]=3)[CH:16]=[CH:17][CH:18]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29][NH:28]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClC(Cl)C>[CH2:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:30][CH2:29][N:28]1[CH2:25][C:21]1[CH:20]=[C:19]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([NH:12][C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[N:3]=[C:2]([CH3:1])[CH:11]=3)[CH:14]=2)[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 70461,2,3,4-TetrahydroisoquinolineHCID 5049666Sodium triacetoxyborohydrideHCID 58958219HCID 58958219, compound

Product 1

HCID 58958113HCID 58958113, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 73 (102 mg, 0.301 mmol) in dichloroethane (3.0 mL) under N2 was added 40 (0.04 mL, 0.315 mmol). The reaction was stirred for 24 minutes before the sequential addition of NaBH(OAc)3 (94 mg, 0.444 mmol) and AcOH (0.02 mL, 0.349 mmol). The reaction was stirred for 19 hours and then extracted with ethyl acetate (2×30 mL). The ethyl acetate extracts were washed with 2 N NaOH (aq. 15 mL), brine (15 mL), dried (MgSO4), and concentrated. The residue was chromatographed on silica gel (dichloromethane to 30:1 to 20:1 dichloromethane/methanol) to give the desired product as a yellow solid (75 mg, 55%).

Workup

  1. extractionextracted with ethyl acetate (2×30 mL)
  2. washThe ethyl acetate extracts were washed with 2 N NaOH (aq. 15 mL), brine (15 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel (dichloromethane to 30:1 to 20:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-3a6b80733b1c44058c9fb9ae5b7042db
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

Loading…