Triethylamine → (1R*,2R*,5S*,6S*)-8-Benzyl-2-(tert-butyldimethylsilyloxy)-6-cyano-1-phenyl-8-azabicyclo[3.2.1]octane

HRID 2088122Notes

Reaction equation

HRID 2088122 reaction equation
FC(F)(F)S([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])(=O)=O.[CH2:16]([N:23]1[CH:28]2[CH:29]([C:31]#[N:32])[CH2:30][C:24]1([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:25](O)[CH2:26][CH2:27]2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>ClCCl>[CH2:16]([N:23]1[C@@H:28]2[C@@H:29]([C:31]#[N:32])[CH2:30][C@@:24]1([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C@H:25]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])[CH2:26][CH2:27]2)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 696847788-Benzyl-6-cyano-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol

Product 1

HCID 69890351(1R*,2R*,5S*,6S*)-8-Benzyl-2-(tert-butyldimethylsilyloxy)-6-cyano-1-phenyl-8-azabicyclo[3.2.1]octane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-Butyldimethylsilyl trifluoromethanesulphonate (23 ml, 76 mmol) was added dropwise to a stirred solution of (1R*,2R*5S*,6S*)-8-benzyl-6-cyano-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol (Description 41; 31 g), triethylamine (18 ml, 243 mmol) in dichloromethane (100 ml) at room temperature over 30 minutes. The reaction mixture was stirred for 15 minutes, quenched with saturated aqueous NaHCO3 and extracted into diethyl ether (3×100 ml). The combined organic extracts were washed with water, brine, dried (Na2SO4) and concentrated to give the title compound.

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. extractionextracted into diethyl ether (3×100 ml)
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4bd1a8f4d0644a89a7e3b784cc77de31
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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