Triethylamine → Benzaldehyde

HRID 1519190Notes

Reaction equation

HRID 1519190 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.C([N:23]1[CH2:30][CH2:29][C:28]2([CH3:34])[C:31]([CH3:33])([CH3:32])[CH:24]1[CH2:25][C:26]1[C:38]([OH:39])=[CH:37][CH:36]=[CH:35][C:27]=12)C1C=CC=CC=1.C(N(CC)CC)C>ClCCCl.CN(C)C1C=CN=CC=1.ClCCl>[CH:38](=[O:39])[C:26]1[CH:27]=[CH:28][CH:31]=[CH:24][CH:25]=1.[CH3:34][C@:28]12[C:31]([CH3:32])([CH3:33])[C@H:24]([NH:23][CH2:30][CH2:29]1)[CH2:25][C:26]1[C:38]([OH:39])=[CH:37][CH:36]=[CH:35][C:27]2=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 67749Trifluoromethanesulfonic anhydrideHCID 66985207HCID 66985207, compound

Product 2

HCID 240BenzaldehydeHCID 10537505HCID 10537505, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic anhydride (9.7 mL) is added to a solution of 3-benzyl-6,11,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-10-ol (13.7 g, the compound may be obtained by reductive amination of benzaldehyde with (2R,6S)-6,11,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-benzo[d]azocin-10-ol and NaHB(OAc)3 in 1,2-dichloroethane), triethylamine (43 mL), and 4-dimethylaminopyridine (50 mg) in dichloromethane (135 mL) chilled to −10° C. under argon atmosphere. The solution is stirred at ca. −5° C. for 30 min and then at room temperature overnight. The solution is added to ice-cold water and then aqueous ammonia solution is added. The resulting mixture is extracted with dichloromethane, the combined organic extracts are washed with water and dried (MgSO4). The solvent is removed under reduced pressure to give the crude product that is used without further purification.

Sources & evidence

ORD record
ord-2a35e77093804639b508e24e03f951e4
Source dataset
uspto-grants-2015_07
Patent number
US09073870B2

Reaction notes

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