(1R,5S)-2beta-formyl-3beta-phenyltropane → (1R,5S)-2beta-n-Butyl-3beta-(p-tolyl)tropane

HRID 1700264Notes

Reaction equation

HRID 1700264 reaction equation
[CH:1]([C@H:3]1[C@@H](C2C=CC=CC=2)C[C@H]2N(C)[C@@H:4]1CC2)=O.[CH:18]([C@H:20]1[C@@H:26]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)[CH2:25][C@H:24]2[N:34]([CH3:35])[C@@H:21]1[CH2:22][CH2:23]2)=O.C([PH3+])C.C([PH3+])CC.[I-].C[N+]1C=CC(C2C=CC=CC=2)=C(O)C=1>C(Cl)Cl>[CH2:18]([C@H:20]1[C@@H:26]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)[CH2:25][C@H:24]2[N:34]([CH3:35])[C@@H:21]1[CH2:22][CH2:23]2)[CH2:1][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 10398938(1R,5S)-2beta-formyl-3beta-phenyltropaneHCID 10610260(1R,5S)-2beta-formyl-3beta-(p-tolyl)tropaneHCID 106866181-Methyl-4-phenyl-3-hydroxypyridinium IodideHCID 18318019Ethyl phosphoniumHCID 18318024Propyl phosphonium

Product 1

HCID 10564066(1R,5S)-2beta-n-Butyl-3beta-(p-tolyl)tropane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using a procedure similar to that described in Example 8, except replacing the compound 18 used therein with compound 19, and replacing the ethyl phosphonium salt with the corresponding propyl phosphonium salt, the title compound 23 was prepared as a colorless oil: [α]25D −76° (c 1.5, CH2Cl2); 1H NMR (CDCl3) δ0.74 (t, 3H, J=7.2 Hz), 0.70-0.90 (m, 2H), 1.12-1.30 (m, 3H), 1.39-1.68 (m, 5H), 1.96-2.20 (m, 3H), 2.24 (s, 3H), 2.31 (s, 3H), 3.03 (dt, 1H, J=5.1 and 13.2 Hz), 3.12-3.20 (m, 1H), 3.20-3.28 (m, 1H), 7.03 (d, 2H, J=8.1 Hz), 7.08 (d, 2H, J=8.1 Hz); 13C NMR (CDCl3) δ14.2, 21.0, 22.7, 24.8, 26.4, 26.7, 30.1, 33.8, 36.0, 42.1, 46.2, 62.1, 64.7, 127.7, 128.7, 135.0, 140.7; MS m/z (%) 271 (M+, 6), 242 (2), 214 (4), 96(40), 83 (100).

Sources & evidence

ORD record
ord-b2ea174af89c472195f4f9e141bdc6f2
Source dataset
uspto-grants-2002_02
Patent number
US06350758B1

Reaction notes

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