Sodium triacetoxyborohydride → HCID 69294561, compound

HRID 1624337Notes

Reaction equation

HRID 1624337 reaction equation
[N:1]1[C:10]2[CH:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]3[C:24](=[O:25])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=[O:26])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.C(O[BH-](O[C:37](=O)[CH3:38])OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:2]([N:1]1[CH:10]=[C:9]([CH3:8])[N:11]=[C:37]1[CH2:38][N:11]([CH:9]1[C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1)[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=[O:26])[CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 589971372-[4-(5,6,7,8-Tetrahydroquinolin-8-ylamino)-butyl]-isoindole-1,3-dione

Product 1

HCID 69294561HCID 69294561, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the above aldehyde (268 mg, 1.773 mmol) and 2-[4-(5,6,7,8-tetrahydro-quinolin-8-ylamino)-butyl]-isoindol-1,3-dione (743 mg, 2.13 mmol) in CH2Cl2 (17 mL) was added sodium triacetoxyborohydride (752 mg, 3.55 mmol). The reaction mixture was stirred at room temperature overnight. Then it was extracted with saturated NaHCO3 (3×20 mL). The organic layer was dried (MgSO4), filtered, concentrated, and dried in vacuo to afford a yellow foam. Purification by flash column chromatography on silica gel using 10% CH3OH/ethyl acetate afforded the product as a pale yellow foam (263 mg, 31%). 1H NMR (CDCl3) (as a mixture of regio-isomers) δ 1.52-1.60 (m, total 4H), 1.89-2.11 (m, total 8H), 2.56-2.66 (m, total 4H), 2.55 (t, 2H, J=7.5 Hz), 3.76 (d, 2H, J=6.0 Hz), 3.99 (t, 1H, J=−6.0 Hz), 4.84-4.90 (m, total 1H) 4.93 and 4.96 (s, total 1H), 5.03-5.06 (m, total 2H), 5.83-5.87 (m, 1H), 6.43 (s, 1H), 6.99 (dd, 1H, J=3.0 Hz), 7.27 (d, 114, J=6.0 Hz), 7.68-7.70 (m, 2H), 7.80-7.82 (m, 2H), 8.39 (d, 1H, J=3.0 Hz).

Workup

  1. extractionThen it was extracted with saturated NaHCO3 (3×20 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customdried in vacuo
  6. customto afford a yellow foam
  7. customPurification by flash column chromatography on silica gel using 10% CH3OH/ethyl acetate

Sources & evidence

ORD record
ord-8f6a01fd250d40358ba9d6c0b4781da2
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

Loading…