HCID 69957837, compound → HCID 69957284, compound

HRID 1937140Notes

Reaction equation

C[O:2][C@H:3]1[C@@H:7]2[CH2:8][C@H:9]3[C@H:14]([C@H:15](/[CH:16]=[CH:17]/[C@@H:18]4[CH2:23][CH2:22][CH2:21][C@@H:20]([CH3:24])[N:19]4[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C@@H:6]2[C@@H:5]([CH3:32])[O:4]1)[CH2:13][CH2:12][CH2:11][CH2:10]3.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>>[CH3:32][C@H:5]1[O:4][C:3](=[O:2])[C@@H:7]2[CH2:8][C@H:9]3[C@H:14]([C@H:15](/[CH:16]=[CH:17]/[C@@H:18]4[CH2:23][CH2:22][CH2:21][C@@H:20]([CH3:24])[N:19]4[C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[C@H:6]12)[CH2:13][CH2:12][CH2:11][CH2:10]3

Participants

Reactant 2

HCID 69957837HCID 69957837, compound

HCID 131709961Jones' reagent

Product 1

HCID 69957284HCID 69957284, compoundYield 97.4%

Procedure

Similarly to Referential example 4, 156.0 mg(0.35 mmol) of (2S,6R)-tert-butyl 2-[(E)-2-[(1R,3R,3aS,4S,4aR,8aS,9aR)-1-methoxy-3-methyl-dodecahydronaphtho[2,3-c]furan-4-yl]vinyl]-6-methyl-1-piperidinecarboxylate were reacted with 0.90 ml of Jones reagent to obtain 147.1 mg of (2S,6R)-tert-butyl 2-[(E)-2-[(3R,3aS,4S,4aR,8aS,9aR)-3-methyl-1-oxo-dodecahydronaphtho[2,3-c]furan-4-yl]vinyl]-6-methyl-1-piperidinecarboxylate, and then 1.00 ml of trifluoroacetic acid was reacted to obtain 113.0 mg of crude (3R,3aS,4S,4aR,8aS,9aR)-3-methyl-4-[(E)-2-[(2S,6R)-6-methylpiperidine-2-yl]vinyl]-3-methyl-decahydronaphtho[2,3-c]furan-1(3H)-one(yield after 2 processes 98%). Then, 0.30 ml of 37% formaldehyde solution and 47.1 mg (2.2 equivalents) of sodium cyanoboronhydride were reacted to obtain 100.8 mg of (3R,3aS,4S,4aR,8aS,9aR)-4-[(E)-2-[(2S,6R)-1.6-dimethylpiperidine-2-yl]vinyl]-3-methyl-decahydronaphtho[2,3-c]furan-1(3H)-one (ent-himbacine)(yield after 3 processes 84%).

Sources & evidence

ORD record: ord-50493b2c7c2d46b095a578cb0d777ac7
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06392059B1

Reaction notes

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