Sodium triacetoxyborohydride → 3-(1,3-Dioxolan-2-yl)propyl 4-((4-((3-(((tert-butoxycarbonyl)amino)(phenyl)-methyl)phenoxy)methyl)piperidin-1-yl)methyl)benzoate

HRID 332714Notes

Reaction equation

HRID 332714 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH:30]([C:32]1[CH:48]=[CH:47][C:35]([C:36]([O:38][CH2:39][CH2:40][CH2:41][CH:42]2[O:46][CH2:45][CH2:44][O:43]2)=[O:37])=[CH:34][CH:33]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([NH:7][CH:8]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:9]1[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=1)[O:15][CH2:16][CH:17]1[CH2:18][CH2:19][N:20]([CH2:30][C:32]2[CH:33]=[CH:34][C:35]([C:36]([O:38][CH2:39][CH2:40][CH2:41][CH:42]3[O:43][CH2:44][CH2:45][O:46]3)=[O:37])=[CH:47][CH:48]=2)[CH2:21][CH2:22]1)=[O:29])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 71113260tert-Butyl(phenyl(3-(piperidin-4-ylmethoxy)phenyl)methyl)carbamateHCID 894066963-(1,3-Dioxolan-2-yl)propyl 4-formylbenzoate

Product 1

HCID 712568613-(1,3-Dioxolan-2-yl)propyl 4-((4-((3-(((tert-butoxycarbonyl)amino)(phenyl)-methyl)phenoxy)methyl)piperidin-1-yl)methyl)benzoateYield 52.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of tert-butyl(phenyl(3-(piperidin-4-ylmethoxy)phenyl)-methyl)carbamate (0.335 g, 0.84 mmol) and 3-(1,3-dioxolan-2-yl)propyl 4-formylbenzoate (0.706 g, 2.67 mmol) in DCM (5 mL), was added sodium triacetoxyborohydride (0.213 g, 1.01 mmol). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with DCM and washed with water, saturated aqueous sodium hydrogen carbonate, and brine. The organic phase was dried with anhydrous magnesium sulfate, and the solvent evaporated at reduced pressure. The residue was triturated with iso-hexane/diethyl ether (3:1) to afford the title compound (0.286 g, 0.44 mmol).

Workup

  1. washwashed with water, saturated aqueous sodium hydrogen carbonate, and brine
  2. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
  3. customthe solvent evaporated at reduced pressure
  4. customThe residue was triturated with iso-hexane/diethyl ether (3:1)

Sources & evidence

ORD record
ord-92facc4fb4f842c1ad2a7ca472dc00e7
Source dataset
uspto-grants-2014_11
Patent number
US08877774B2

Reaction notes

Loading…