Diethyl Ether → HCID 118415268, compound

HRID 1775779Notes

Reaction equation

HRID 1775779 reaction equation
[C:1]([O:5][C:6]([O:8][Si](C(C)(C)C)(C)C)=[CH2:7])([CH3:4])([CH3:3])[CH3:2].[CH2:16]([N:23]([CH3:35])[C@@H:24]([CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)[CH:25](OC)[O:26][CH3:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.B(F)(F)F.CCOCC>ClCCl.CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[CH2:8][C@@H:25]([O:26][CH3:27])[C@@H:24]([N:23]([CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH3:35])[CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1)([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6356Boron trifluorideHCID 10922347(1-tert-Butoxy-vinyloxy)-tert-butyl-dimethyl-silaneHCID 118415298HCID 118415298, compound

Product 1

HCID 118415268HCID 118415268, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To (1-tert-butoxyvinyloxy)(tert-butyl)dimethylsilane (7) (9.9 g, 43.0 mmol) in dichloromethane (80 mL) was added (S)—N-benzyl-1-cyclopentyl-2,2-dimethoxy-(S)—N-benzyl-1-cyclopentyl-2,2-dimethoxy-N-methylethanamine (6) (8.0 g, 28.8 mmol) followed by a solution of BF3. ether (3.6 mL) in DMF (4.9 mL) and dichloromethane (20 mL) at 0° C. The reaction mixture was stirred at room temperature overnight. After concentrated, the residue was purified by silica gel flash chromatography (petroleum ether:ethyl acetate, 10:1) to give product 8 (4.3 g, 66%). LC-MS: 361.3 [M+H+]+.

Workup

  1. customat 0° C
  2. concentrationAfter concentrated
  3. customthe residue was purified by silica gel flash chromatography (petroleum ether:ethyl acetate, 10:1)

Sources & evidence

ORD record
ord-318e08feda5e4e6782a772d5aae8add1
Source dataset
uspto-grants-2016_02
Patent number
US09260478B2

Reaction notes

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