Propionic Acid → (6aR,9R,10aR)-3-Methoxy-5,6,6,9-tetramethyl-5,6,6a,7,8,9,10,10a-octahydro-phenanthridine

HRID 1451707Notes

Reaction equation

HRID 1451707 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11](O)[CH2:12][C@H:13]([CH3:20])[CH2:14][CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18].C1(B(O)O)C=CC=CC=1.C(O)(=O)CC.COC1C=CC2C3C(C(C)(C)N(C)C=2C=1)CCC(C)C3>C1C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:10][O:9][C:7]1[CH:6]=[CH:5][C:4]2[C@H:11]3[C@H:16]([C:17]([CH3:19])([CH3:18])[N:2]([CH3:1])[C:3]=2[CH:8]=1)[CH2:15][CH2:14][C@@H:13]([CH3:20])[CH2:12]3

Participants

7

Reactant 4

HCID 1032Propionic AcidHCID 66827Phenylboronic AcidHCID 15208596(3R)-1-(2-methylamino-4-methoxy-phenyl)3,7-dimethyl-oct-6-en-1-olHCID 152086023-Methoxy-5,6,6,9-tetramethyl-5,6,6a,7,8,9,10,10a-octahydro-phenanthridine

Product 1

HCID 9881987(6aR,9R,10aR)-3-Methoxy-5,6,6,9-tetramethyl-5,6,6a,7,8,9,10,10a-octahydro-phenanthridine

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6212ChloroformSolvent

Procedure

A mixture of (3R)-1-(2-methylamino-4-methoxy-phenyl)3,7-dimethyl-oct-6-en-1-ol (291 mg, 1 mmol), phenylboronic acid (365 mg, 3 mmol) and propionic acid (22 rag, 0.3 mmol) in benzene (10 mL) was refluxed for 20 h to give, after chromatography, 140 mg (51%) of (6aR,9 R, 10aR)-3-methoxy-5,6,6,9-tetramethyl-5,6,6a,7,8,9,10,10a-octahydro-phenanthridine: [α]D +37 (c 4.5, CHCl3); 1H nmr (400 MHz, CD3COCD3), δ 0.83 (q, 1H, J=11.6 Hz, H-10ax), 0.98 (d, 3H, J=6.5 Hz), 1.0 (s, 3H), 1.20 (m, 2H), 1.22 (m, 1H), 1.29 (s, 3H), 1.54 (m, 1H), 1.82 (m, 1H), 1.89 (m, 1H), 2.37 (dr, 1H, J=10.3, 2.7 Hz), 2.45 (m, 1H), 2.83 (s, 3H), 3.71 (s, 3H), 6.12 (d, 1H, J=2.4 Hz), 6.16 (dd, 1H, J=8.3, 2.4 Hz), 7.0 (d, 1H, J=8.3 Hz); 13C nmr (100.6 MHz, CD3COCD3), δ 19.1, 23.1, 26.5, 28.7, 32.4, 33.0, 35.8, 36.0, 41.3, 48.9, 55.1, 57.7, 99.2, 100.7, 120.2, 125.9, 147.8, 160.0. Exact Mass calcd. for C18H28NO (M+1): 274.2170; found: 274.2172.

Workup

  1. temperaturewas refluxed for 20 h
  2. customto give

Sources & evidence

ORD record
ord-3dbecdbd311d4d048131b41a066d2d6f
Source dataset
uspto-grants-1997_02
Patent number
US05605906

Reaction notes

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