Sodium triacetoxyborohydride → HCID 71112545, compound

HRID 1472757Notes

Reaction equation

HRID 1472757 reaction equation
[OH:1][C:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]([O:5][CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)=[O:4].[O:25]1[CH2:29][CH2:28][O:27][CH:26]1[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][O:35][C:36]1[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][CH:37]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[OH:1][C:2]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:3]([O:5][CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:40][C:39]2[CH:38]=[CH:37][C:36]([O:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH:26]3[O:25][CH2:29][CH2:28][O:27]3)=[CH:43][CH:42]=2)[CH2:9][CH2:8]1)=[O:4]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 71093464HCID 71093464, compoundHCID 86676461HCID 86676461, compound

Product 1

HCID 71112545HCID 71112545, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of piperidin-4-ylmethyl 2-hydroxy-2,2-diphenylacetate (0.4 g, 1.23 mmol) and 4-((5-(1,3-dioxolan-2-yl)pentyl)oxy)benzaldehyde (0.38 g, 1.44 mmol) in DCM (5 mL) was added sodium triacetoxyborohydride (0.388 g, 1.83 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was partitioned between EtOAc and saturated sodium hydrogen carbonate. The organic phase was dried (sodium sulfate), filtered, and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography eluting with 1 to 10% methanol in ethyl acetate to afford the title compound as a colourless oil (0.50 g, 26%).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and saturated sodium hydrogen carbonate
  2. dry with materialThe organic phase was dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material was purified by silica gel column chromatography
  6. washeluting with 1 to 10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-fdff5b2b358b44d0a060dcbea15e4be6
Source dataset
uspto-grants-2015_04
Patent number
US09012644B2

Reaction notes

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