Methanol → HCID 86635310, compound

HRID 656853Notes

Reaction equation

HRID 656853 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](=[O:16])[N:10]2[CH2:13][CH:14]=O)=[CH:5][CH:4]=1.[O:17]1[C:26]2[CH:25]=[C:24]([CH2:27][N:28]([CH:36]3[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]3)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[N:23]=[CH:22][C:21]=2[O:20][CH2:19][CH2:18]1.CO.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)(Cl)Cl>[O:17]1[C:26]2[CH:25]=[C:24]([CH2:27][N:28]([CH:36]3[CH2:41][CH2:40][N:39]([CH2:14][CH2:13][N:10]4[C:11]5[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=5)[CH:7]=[CH:8][C:9]4=[O:16])[CH2:38][CH2:37]3)[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[N:23]=[CH:22][C:21]=2[O:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 887MethanolHCID 5049666Sodium triacetoxyborohydride2×HCID 578154611,1-Dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-4-piperidinylcarbamate2×HCID 59397833(7-methoxy-2-oxoquinolin-1(2H)-yl)acetaldehyde

Product 1

HCID 86635310HCID 86635310, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of [7-(methyloxy)-2-oxo-1(2H)-quinolinyl]acetaldehyde (65 mg, 0.3 mmol) and 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-4-piperidinylcarbamate (for a synthesis see WO2004/058144 Example 99(h)) (105 mg, 0.3 mmol) in chloroform (3 ml) and MeOH (3 ml) was stirred at rt for 1 h. The mixture was then treated with NaBH(OAc)3 (190.8 mg, 0.9 mmol), stirred at rt for 0.5 h. 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-4-piperidinylcarbamate (52 mg, 0.15 mmol) and NaBH(OAc)3 (127 mg, 0.6 mmol) were added and the reaction stirred at rt for 1 hour. The solvents were then removed and the residue was subjected to column chromatography on silica gel eluting with 0-10% methanol-DCM to afford the desired compound (92 mg, 56%).

Workup

  1. stirringthe reaction stirred at rt for 1 hour
  2. customThe solvents were then removed

Sources & evidence

ORD record
ord-49858017a8d342a18aabbcf56c47f394
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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