2,2-diethylbutanoyl Chloride → (4R,6R)-6-{2-[(1S,2S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-8-(2.2-diethylbutyryloxy)-2-methyl-1-naphthyl]ethyl}-tetrahydro-4-hydroxy-2H-pyran-2-one

HRID 2399979Notes

Reaction equation

HRID 2399979 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](C(C)(C)C)(C)C)[CH2:15]2)=[CH:5][CH2:4][CH2:3]1.[CH2:30]([C:32]([CH2:38][CH3:39])([CH2:36][CH3:37])[C:33](Cl)=[O:34])[CH3:31]>>[CH2:30]([C:32]([CH2:38][CH3:39])([CH2:36][CH3:37])[C:33]([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]([OH:21])[CH2:15]2)=[CH:5][CH2:4][CH2:3]1)=[O:34])[CH3:31]

Participants

3

Reactant 2

HCID 50970172,2-diethylbutanoyl ChlorideHCID 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 22856164(4R,6R)-6-{2-[(1S,2S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-8-(2.2-diethylbutyryloxy)-2-methyl-1-naphthyl]ethyl}-tetrahydro-4-hydroxy-2H-pyran-2-oneYield 61.6%

Procedure

A procedure similar to that described in Example 6, above, was followed, but using 1.26 g (3.0 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-butyl-dimethylsilyloxy-2H-pyran-2-one [prepared as described in Japanese Patent Kokai Application No. Sho 59-175450] and 2.22 g (13.6 mmol) of 2,2-diethylbutyryl chloride, to provide 800 mg of the title compound.

Sources & evidence

ORD record
ord-bce8e485ab8b445384680aa3eb4bd35b
Source dataset
uspto-grants-1995_09
Patent number
US05451688

Reaction notes

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