Acetate → HCID 23260664, compound

HRID 2248084Notes

Reaction equation

HRID 2248084 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([O:13][CH3:14])=[C:5]([CH2:15][CH:16]2[CH2:21][CH2:20][C:19]([CH:23]([OH:25])[CH3:24])([OH:22])[CH2:18][CH:17]2[C:26]([O:28]CC2C=CC=CC=2)=O)[CH:4]=1.C(OC(=O)C)(=O)C.C([O-])(=O)C.C1CCCCC=1>CN(C)C1C=CN=CC=1.[Pd].N1C=CC=CC=1>[OH:25][CH:23]([C:19]1([OH:22])[CH2:20][CH2:21][CH:16]2[CH:17]([C:26](=[O:28])[C:4]3[C:5]([CH2:15]2)=[C:6]([O:13][CH3:14])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=3[O:2][CH3:1])[CH2:18]1)[CH3:24]

Participants

8

Reactant 4

HCID 175AcetateHCID 7918Acetic AnhydrideHCID 8079CyclohexeneHCID 19816459HCID 19816459, compound

Product 1

HCID 23260664HCID 23260664, compoundYield 66.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Procedure

Operation as described in Example 6, 0.44 g of 1-(1,4-dimethoxy-3-naphthylmethyl)-2-benzyloxycarbonyl-4-(1-hydroxyethyl)-4-hydroxyl-cyclohexane, prepared as described in Example 11, was treated with acetic anhydride in presence of 4-dimethylamino-pyridine and pyridine. The corresponding acetate was treated with cyclohexene in the presence of 10% by weight palladium-on-carbon in order to remove the benzyl group. The acid was cyclized by treatment with a mixture of trifluoroacetic anhydride and trifluoroacetic acid at 0° C. Finally the removal of the acetyl O-protecting groups by treatment with sodium methylate afforded. after purification by chromatography on a silica gel column, 0.225 g of the title compound (overall yield 66%); IR (film): 3450 cm-1 (OH), 1675 cm-1 (C=O, benzylic ketone). PMR (CDCl3): inter alia δ 1.3 (d, J=4 Hz, CH3 --CH), 1.6-3.5 (m, 3H), 3.85 (s, OCH3), 3.90 (s, OCH3), 7.2-8.4 (m, four aromatic H).

Workup

  1. customprepared
  2. customto remove the benzyl group
  3. additionThe acid was cyclized by treatment with a mixture of trifluoroacetic anhydride and trifluoroacetic acid at 0° C
  4. customFinally the removal of the acetyl O-protecting groups by treatment with sodium methylate
  5. customafforded

Sources & evidence

ORD record
ord-7525589b468140f092612c19f33bdebd
Source dataset
uspto-grants-1991_08
Patent number
US05037970

Reaction notes

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