Valproic Acid → (4R,6R)-6-{2-[(1S,2S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-8-(2-propylvaleryloxy)-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one

HRID 400157Notes

Reaction equation

[OH:1][C@@H:2]1[C@H:11]2[C:6]([CH:7]=[CH:8][C@H:9]([CH3:29])[C@@H:10]2[CH2:12][CH2:13][C@H:14]2[O:19][C:18](=[O:20])[CH2:17][C@H:16]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:15]2)=[CH:5][CH2:4][CH2:3]1.[CH2:30]([CH:33]([CH2:37][CH2:38][CH3:39])[C:34](O)=[O:35])[CH2:31][CH3:32]>>[CH2:30]([CH:33]([CH2:37][CH2:38][CH3:39])[C:34]([O:1][C@@H:2]1[C@H:11]2[C:6]([CH:7]=[CH:8][C@H:9]([CH3:29])[C@@H:10]2[CH2:12][CH2:13][C@H:14]2[O:19][C:18](=[O:20])[CH2:17][C@H:16]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24])[CH2:15]2)=[CH:5][CH2:4][CH2:3]1)=[O:35])[CH2:31][CH3:32]

Participants

Reactant 2

HCID 3121Valproic Acid

HCID 53731106(4R,6R)-6-{2-[(1S,2S,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one

Product 1

HCID 57259788(4R,6R)-6-{2-[(1S,2S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-8-(2-propylvaleryloxy)-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-oneYield 99.1%

Procedure

A procedure similar to that described in Example 3, above, was followed, but using 1.0 g (2.4 mmol) of (4R,6R)-6-{2-[(1S,2S,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Japanese Patent Kokai Application No. Sho 59-175450] and 686 mg (4.8 mmol) of 2-propylvaleric acid, to provide 1.3 g of the title compound.

Sources & evidence

ORD record: ord-207879f1fa9d478aa9118b54394a76dc
Source dataset: uspto-grants-1998_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05827855

Reaction notes

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